≡ Menu

The 3 Biggest Problems with Portland


The 3 Biggest Problems with PortlandI’m going off topic today because life isn’t all about money, right? We live in Portland and long time readers would know that I love Portland. I moved to Portland in 1996 to work for the Megacorp. It was a rough transition at first because I went to college in sunny Santa Barbara, CA. The abrupt transition from perfect weather to 8 months of drizzle per year was depressing to say the least. I got over it and came to love Portland, though. Portland has hit its stride over the past 5-6 years and it has been a perennial in many travel magazine’s “best cities” lists. The tourism boom is great for the local economy and tourists spent nearly $5 billion last year.

Portland is a great place to live, but it has changed a lot over 20 years. When I first moved here, Portland felt like a quaint small city. There wasn’t a lot of violent news on TV. The traffic was not too bad. Life was lived at a relaxed pace. Now, Portland feels more like a big city. There are shootings, stabbings, and other violent crimes on the news every day. The streets are full of cars and traffic jams are getting worse. The pace of life is still more relaxed than CA, but I can feel it ramping up. Part of it is probably because I’m getting older and grumpier. My theory is life always seems better in your 20’s because you were young, idealistic, and healthy. Crime has actually declined considerably over the past 20 years according to statistics. Maybe I didn’t pay much attention to the news back then.

Anyway, I still love Portland, but I’m dreaming more and more about our RB40 villa. Oregon has been the number 1 moving destination for the past 3 years and it’s getting a little crowded around here. More people means more problems after all. Portland metro has grown by 600,000 people since I moved here and the forecast predicts 750,000 more people in the next 20 years.  The current population is around 2,400,000 people and we are the 23rd largest metro in the US. That is pretty big. The problems in Portland are also becoming more noticeable. Problems are growing and the local government does not know how to deal with them. Lately, Portland is starting to disappear from the “best cities” list. Tourists are noticing the visible problems and the shine is wearing off. We don’t want to move while RB40Jr is in school so we will be here for many years. However, if the problems keep getting worse, we may have to move up our timeline.


Portland has a huge homeless population. This is one of the first things tourists notice about Portland. Visitors arrive at the airport, take the light rail to downtown, and they inevitably get asked for money. Even our governor was ‘stunned’ by the number of campers in Portland when she came to town. Oregon’s homeless population rose by nearly nine percent last year. That’s a much bigger percentage increase than Washington and California.

The problem is so bad that the mayor recently declared an emergency and instituted the “safe sleep” policy. This allows the homeless to camp in groups of up to six, from 9 pm to 7 am. Predictably, camps sprang up like dandelions given free rein.  There are camps on the sidewalks, under the bridges, bicycle corridor, next to the freeway entry ramps, and basically any flat space with some overhead shelter. We lived downtown for years and the homeless problem has never been more visible. The camps are strewn with garbage, crimes are increasing, drug use is rampant, and they become a semi-permanent encampment. Nobody wants to pack up at 7 am and leave. The cops are not enforcing the rule because they don’t want to get into a violent altercation. The local businesses are suing the city over the policy and it’s a huge debacle. This policy seems like an experiment gone wrong.  The incoming mayor said he won’t support this policy so at least it is short term.

Here is a picture I took while I was driving around on Thursday. Sorry, the focus was off, but you get the idea.

homeless camp

Anecdotally, the numbers of homeless camps seem to be decreasing in the downtown area. Over the last few weeks, I’ve seen camps disappear and chain link fences erected under some bridges. Perhaps the cops have started making people pack up in anticipation of summer. The nicer weather usually means an explosion of homeless “travelers” that comes to Portland to take advantage of the social services. Maybe they are trying to head that off.

The homeless people have never bothered me much. The panhandlers are very good at picking out local residents. They rarely bother the locals because we rarely give cash. We are desensitized and it’s better to donate to shelters, food banks, and local non profits. Many homeless people have drug problems and cash won’t help them. Personally, I don’t mind the panhandling (which I simply say no to), but many tourists are targeted by aggressive panhandlers. Who wants to pay $300 per night and see a bunch of homeless people? It doesn’t jive with their image of Portlandia.

The homeless problem seems to be getting worse over the last few years because the cost of living here is increasing rapidly. Mobile home parks are getting sold to developers. Tenants are getting evicted for no reason so the landlords can remodel and raise the rent. New glitzy apartments are being built all across the city, but there are very few affordable units. The increased cost of living pushed many people over the edge. People with fixed income have nowhere to go when their trailer park or apartment complex closes down. They can’t pay $20,000 to move their manufactured home to a new site. It’s a tough environment to be on the edge.

Okay, I’ve gone on long enough about this problem. The local government doesn’t know how to fix it and I don’t either. They are trying to build more shelters, but that will take time and money. Seems to me, the problem will keep getting worse as the cost of living continues to increase. We’ll probably allow more encampments in out of the way locations like the Dignity Village near the airport.

Graduation Rate

In 2013, Oregon’s on time graduation rate (4 years) was the lowest of any state in the country at 69%. We have improved to 74% since then, but a big part of the improvement is due to the revised definition of “graduates.” Apparently, some students stay in high school an extra year even after they completed 4 years of education. The schools count the students as enrolled and continue to receive funding from the state. The money is used to pay for a year of community college, books, and counseling. It is a win-win because the schools receive more resources and the students get a free year of education. Well, maybe it’s not a win-win for the tax payers… Students in this category are now considered on time graduates. This sounds like a good program to me.

Our high school is in a good area and the graduation rate is way better at 93%. I’m still baffled as to why the overall graduation rate in Oregon is so low. High school is not that difficult and everyone should be able to graduate on time. I understand some students have problems at home, but 1 out of 4 kids not graduating on time seems ridiculous to me. If RB40Jr starts down that path, we’re outta here.


Portland has been a popular city for many years now and we are starting burst at the seams. In Oregon, we don’t like urban sprawl and we minimize it with the “urban growth boundary.” The area inside the UGB is targeted for higher density urban development and the area outside is reserved for agriculture and nature. The UGB made Portland a dense compact metro and gave us a unique feel. One big reason why I love living downtown is that we can get to any part of the city in less than 30 minutes from our home, assuming light traffic. Drive out a little more and you’ll be surrounded by trees and greenery. I never liked Southern California because you can drive for hours and still be surrounded by urban sprawl. There are just so many people living in California.

The traffic jam is getting worse here. Portlanders do not like freeways and we haven’t built a new freeway since 1983. The local government invested heavily in public transportation instead. I love our public transportation system, but it doesn’t work for everyone. Most people still drive and our freeways can’t accommodate the increased traffic. Luckily, I don’t have to go to work anymore and I avoid the freeways during rush hour like the plague.

Portland is starting to feel more crowded lately. We are getting bigger and bigger every year. There are apartment construction projects in every neighborhood. Our schools are getting slammed. The school board is in the process of redistricting the school boundary to relieve the most overcrowded schools. Portland doesn’t feel like a small city anymore. It is a big city with big cities’ problems. Portland was just the perfect size for me in the 90’s, but now it’s starting to get too big. Hopefully, the problems don’t worsen much over the next decade. We still like Portland and aren’t ready to move quite yet.

Whew, I went on a bit too long about the homeless problem, didn’t I? How are things in your neighborhood? Do you have similar problems in your area?

Check out this beautiful promotional video from Travel Portland.

Image  by Alejandro Rdguez

The following two tabs change content below.
Joe started Retire by 40 in 2010 to figure out how to retire early. He spent 16 years working in computer design and enjoyed the technical work immensely. However, he hated the corporate BS. He left his engineering career behind to become a stay-at-home dad/blogger at 38. At Retire by 40, Joe focuses on financial independence, early retirement, investing, saving, and passive income.

For 2018, Joe plans to diversify his passive income by investing in US heartland real estate through RealtyShares. He has 3 rental units in Portland and he believes the local market is getting overpriced.

Joe highly recommends Personal Capital for DIY investors. He logs on to Personal Capital almost daily to check his cash flow and net worth. They have many useful tools that will help every investor analyze their portfolio and plan for retirement.

Latest posts by retirebyforty (see all)

Get update via email:
Sign up to receive new articles via email
We hate spam just as much as you
{ 59 comments… add one }
  • Pennypincher June 24, 2016, 4:34 am

    Wow, Joe. I say “Keep Portland Weird!”-ha, ha. Seriously, it sounds as if you may want an “out”, an “exit strategy”, a “plan B” when RB40jr is done with school and out on his own.
    Let me tell you this, I used to think that street people were “benign” and I would practically step over them on my way to work in the morning. No longer. We were assaulted by a street person in CA on vacation. It was awful, traumatic. He got 7 years in prison for his actions.
    I think it’s gone too far. I also have very little tolerance for crime, and moved farther out of my town because of it. Cities will grow/change. They have to for economic growth. Economic growth = survival. The traffic has gotten so bad where I live, I see myself raising the white flag of surrender once again, and moving someday.
    On a more upbeat note- I love Portland. When I visit there, the people are so very friendly, open and honest. Besides, Oregon is green, lush, gorgeous!

    • retirebyforty June 24, 2016, 10:24 am

      I plan to walk the earth when RB40Jr is out on his own. Not sure if Mrs. RB40 will do that. She might join me for a while and head back home periodically. 🙂
      Homeless people here are generally harmless. You still have to watch yourself, though. Many has drug problems and/or mental heath issues. You don’t know what they’ll do next. Violent crime is still not too bad here, but property crimes are very high. I love the lushness here. It’s depressing to see the brown hills in CA when we go back to visit.

  • The Green Swan June 24, 2016, 4:56 am

    I feel like many of these problems are common for up and coming cities. That is really too bad about the panhandlers, it can be such a black eye for an otherwise nice and clean city. I like the idea of limiting the sprawl, but I can see how overcrowding could result.

    Here in Charlotte, another up and coming city, we have a few similar problems. I’m not sure what our graduation rate is, but I know we live in a great school district. Public transportation has been a big issue. We have a bus system which is ok, but the light rail only goes north and south and it isn’t connected to the airport.

    We hear about a fair amount of crime, but not a ton and I don’t think it has gotten any worse since we moved here 5 years ago. And panhandlers aren’t a huge issue, but there are some around.

    Overall though, I really like Charlotte. It is a fairly “new” city with a lot of construction and development in the last 15 years and is kept pretty clean. Plus, coming from the North, the weather is much better! 🙂

    • retirebyforty June 24, 2016, 10:27 am

      Normal panhandling is fine with me, but some of them are very aggressive. It’s too bad tourists have to put up with this. Many people complained to the travel board and said they’ll never come back.
      Charlotte sounds nice. Wow, I just checked and Charlotte is bigger than Portland. It’s probably more spread out.

  • Apathy Ends June 24, 2016, 5:04 am

    Not many homeless people in Minneapolis, at least on the routes I take around the city – I have never seen a camp like the one in the picture.

    Aggressive panhandling is a nuisance, I don’t mind (don’t have any problems saying no) but a lot of Midwesterners lack that skill and I’m sure they give when approached

    Depending on the year traffic can be miserable, we only have 6 months to do road construction so it gets packed in

    • retirebyforty June 24, 2016, 10:28 am

      Minneapolis is too cold to be homeless in. 🙂

  • Mr. Tako @ Mr. Tako Escapes June 24, 2016, 5:10 am

    Hi Joe.
    This sounds like the same story we have up in the Seattle area — Lots of people, too many homeless, and terrible traffic.
    We are actually thinking about moving to the Portland area because the problems don’t seem as bad as Seattle’s. Maybe I need to re-evaluate that. It could have changed in the last few years when I wasn’t looking.
    Real Estate prices also seem cheaper in Portland compared to we encounter ‘up North’. My next door neighbor’s home just sold for $750,000.

    • retirebyforty June 24, 2016, 10:30 am

      I still think Portland is nicer than Seattle. Seattle is way too busy now.
      You should visit and check it out. Many areas are still nice, but close in neighborhoods are getting overrun by homeless people.
      It definitely gotten worse over the past few years. Portland is more compact so I think that’s why the homeless problem is more visible.

      • Casey W June 27, 2016, 2:23 am

        Portland has similar problems to San Francisco: compact with homeless flocking there for social services. San Fran is a beautiful city and I day dream all the time about living in a high-rise condo, but I can’t get over how many crazy homeless people are in San Fran. San Fran has been cracking down on homeless camps like crazy this past month or so after a fatal shooting–the mayor declared all homeless camps unsafe. I wonder if Portland will end up in a similar city-wide crackdown.
        Sad to see so much homelessness. No idea what to do about it. All I know if San Fran and Portland would feel a lot safer and look a lot nicer with less homeless.

        • retirebyforty June 27, 2016, 9:57 am

          Thanks for the SF update. We had more crimes recently too. There were shooting, stabbing, arson, and who knows what else. It’s not safe when people are so desperate.

  • Gwen @ Fiery Millennials June 24, 2016, 5:46 am

    You know, I complain about living in the Midwest but now it doesn’t seem too bad. The only traffic jams we have around here are when a tractor is on the road and cars stack up behind it. Cost of living and crime are also pretty low! I remember being shocked the first time I saw a homeless person. I was 18!

    • retirebyforty June 24, 2016, 10:31 am

      Our kid has seen homeless people all his life. We try to teach him more about it, but it’s hard to understand when you’re small.

  • Believe Fire June 24, 2016, 5:48 am

    Thanks for sharing Joe. I’ve only been to Portland once, but it wasn’t too long after you moved there. At the time I thought it was a beautiful place, and I’m sure it still is in many ways. It’s a shame to hear about the problems occurring and the negative direction the city could be headed in. Good luck toughing it out until RB40jr is out of school.

    • retirebyforty June 24, 2016, 10:31 am

      Portland is still beautiful and I still love it here. Hopefully, we can improve over the next 13 years. It’s good now, but I don’t want it to get worse.

  • Pia @ Mama Hustle June 24, 2016, 6:15 am

    It seems the homeless population is rising all over. I wonder what’s causing that? In Atlanta, it’s spreading out into the suburbs, which I feel like it didn’t when we moved here in the late 90s. Then again, at that point, a lot of these suburbs didn’t exist.

    • retirebyforty June 24, 2016, 10:33 am

      Actually, homelessness has declined overall, but it’s increasing on the West Coast. I’m sure the higher cost of living is a big part of this.

  • Frugal Familia June 24, 2016, 7:20 am

    No place is perfect and there’s always going to be things that can be improved upon. To me the issues you point out seem relatively minor, maybe it’s because I live in Chicago and my top 3 would be gun violence/crime, highest property tax rate in the country, and some of the worst traffic in the country.

    • retirebyforty June 24, 2016, 10:33 am

      Right. I don’t want to live in a bigger city like Chicago. Portland was the perfect size and I don’t want it to get a lot bigger.

  • Susan June 24, 2016, 7:47 am

    I live in Phoenix AZ, have for 23 years now. Moved her because it seemed like Camelot, and it was for a long time. I’ve managed to have decent jobs, make good salaries, owned and sold a few homes, but there’s still homelessness, high teen pregnancy rate, high school drop out rate is high. I grew up in NYC and thought that was an amazing place to grow up, believe it or not I felt safe there because everyone knew everyone. In phoenix you don’t know your neighbors. The garage goes up, your car goes in and your garage comes down. you hang out in your back yard. I think tax money could be better spent on drug prevention, rather than treatment. If you never do it you won’t get addicted.
    Bottom line is Camelot does not exist.

    • Pennypincher June 24, 2016, 10:06 am

      Had to comment, Susan- Very interesting observation about the garage doors go up, cars go in, doors go down- spot on! The police in our community even mentioned how nobody knows their neighbor. We need to go back to the front porch days when people would stop, visit neighbors sitting out on their porches. Working parents today are too busy w/work, commute, kids, etc. No time to socialize unless organized.

    • retirebyforty June 24, 2016, 10:35 am

      People here are pretty neighborly. We live in a condo and knows some neighbors, not everyone though. The garage thing is true in the suburb. People are a lot more isolated now.

  • David Michael June 24, 2016, 7:59 am

    Portland and Portlandia. Beautiful towns…not so perfect anymore in our country of the USA which is not so perfect as well.

    I moved to Eugene 32 years ago from Palo Alto, which was crowded, too expensive, and way too sunny for me. Most of all, I hated the freeway traffic and snarl. The move to Eugene was perfect at the time with a population of 80,000. Today, it’s going nuts with people moving here. Now we have over 250,000 in the Eugene-Springfield area. Not too much traffic deadlock but the crowds (zombies) are coming, coming, coming. I try to tell eveyone it rains here…all the time. (Actually only about seven months.) One of our biggest problems…homeless. It seems to be using up the resources of our city trying to figure out what to do with over 4000 people camping in designated areas. Tiny houses are now being constructed for the vets.

    It’s a sign of our times that things are not working. Governor Reagan closed the mental institutions in California and then did the same thing nationwide as President. The results have trickled down to most cities in the way of homelessness but also recent shootings. We need more than adequate housing, the entire country needs a better educational system and especially universal healthcare. Otherwise, every major city in the US is going to feel the effects of the unemployed. Otherwise, I still love Eugene, mainly because of the UO Ducks and the fact I can be on my favorite trout streams in the matter of 20 minutes. Not too shabby!

    • retirebyforty June 24, 2016, 10:37 am

      I hate the freeway traffic too. Eugene is still much smaller than Portland. The traffic doesn’t seem bad. I guess it depends on where you’re coming from. Homelessness is a growing problem on the west coast. It’s tough because once you’re there, it’s really hard to get out of that situation. I think universal healthcare would help as well.

  • Eric June 24, 2016, 8:40 am

    The fix for almost every problem mentioned is to build more housing. Housing costs are the reason that so many are on the streets and the reason that expenses are going up so much.

    You said yourself that you enjoy the lack of sprawl, but that limits where people can live. Building up is obviously more expensive, but at least regulations in Portland allow some development, unlike most of California.

    The upside to more housing is that it lowers the #1 expense of Americans. (The expense that is 2x larger than any other expense.) The downside is that it creates more traffic. Driverless taxis will be here in the next 5 years and start to solve the traffic issue.

  • Pennypincher June 24, 2016, 10:09 am

    Need to comment here-yes, the younger generation needs to know about Reagan closing all the mental institutions, w/no real options or solutions, and the trickle effect has been this never ending homelessness. Glad you brought this up.

  • Andrew June 24, 2016, 11:19 am

    I read in the news recently about the homelessness problems in Portland. The camps reminded me of “The Jungle” in Seattle which is a homeless encampment underneath a highway where crime often occurs. Often times these same issues come up in big cities, here in NYC homelessness and overcrowding are constant problems with no clear solution.

    • retirebyforty June 25, 2016, 11:11 am

      Crime seems to be on the rise here as well. Previously, I don’t hear much about crimes, but now there are a few every week. I think they are mostly within the circle. Homeless against homeless…

  • Jad June 24, 2016, 11:32 am

    Interesting to think about many of the statistics you have mentioned. I live in St. Louis which is an extremely bifurcated metro area. In the western portion of the metro area there is basically no crime and high school graduation rates are above 95%. The actual city itself is a totally different story there can be shootings every day and the graduation rate is below 50%. I live in the western portion of the metro area which is insulated from the problems of the city. I was actually shocked by the Ferguson, Missouri fiasco because I was totally unaware of problems that emanated from that area.

    Anyways St. Louis is frequently listed as one of the cheapest places to live in America. A 1500 square foot 3/2 can go for $1200 or less in good areas. I have 4 friends who rent out said apartment (one lives in the fairly large basement area) for $300/month/person. The same unit could literally be 3-4x that price on the coasts. Most large cities in the U.S. offer many of the same basic opportunities and if that’s enough for you, give St. Louis or other Midwest or southern towns a shot.

    Jobs on the coasts will pay more but who cares? Its not what you make its what you save. You can live like a king on a $50k/year salary.

    • retirebyforty June 25, 2016, 11:16 am

      Wow, the cost of living is very low there. It would be tough to find a 1 bedroom apartment for less than $1,200.
      Portland is kind of like that. The west side has better graduation rates and less crimes. We’re in downtown which is in the middle. A lot of property crime, but not much violent crimes.

  • L June 24, 2016, 12:53 pm

    Your 3 biggest problems are also some of mine. We also live in Portland, but not downtown. A part of our retirement plan is to move us out farther to the burbs or country even, another part of the state, or another state entirely. I want peace and quiet and a 20 minute drive when I need to go somewhere. We also can buy our home outright, because its cheaper everywhere else. Plus there are more beautiful open spaces. I had this where I used to live for most of my life. It’s a city in Oregon. It has its problems, but not as bad as Portland yet. Commute costs/higher rent or mortgage/food costs are big reasons to move farther away. It would actually give us more freedom faster. I know a lot of retirement sites say live in the big city. I find it easier/cheaper to live in a small city or the country and visit the big city once in awhile for fun. I hope to semi-retire us in the next 5 years! Love the blog by the way!

    • retirebyforty June 25, 2016, 11:19 am

      I hear you. When we move, we probably would go for the rural area and try to get a bigger property. Portland is nice, but it’s getting crowded. I don’t like the suburb, though…
      My mom stays with us 6-8 months out of the year and she likes it in Portland. It’s easy for her to get around. When she is with my brothers, it’s much more difficult because she doesn’t drive.
      Thanks for the compliment!

  • Fiscally Free June 24, 2016, 1:59 pm

    Those sound like the same problems I complain about.
    I have no tolerance for homeless people. I shouldn’t have to deal with being harassed when I’m walking down the street or putting gas in my car, and I really don’t want my wife or child to be harassed.
    I know many homeless people have mental issues, so I don’t really blame them. We need to do better as a society when it comes to getting them help.

  • K June 24, 2016, 5:55 pm

    sigh… have you been to Seattle lately? It’s so sad and so bad. I drive around a lot for my job and I just can’t believe what I see. There are so many homeless people, so many! and laying around all day. Like they are camping. One guy was laying on the sidewalk with his feet up in the air. They sit around on chairs and have barbecues and watch the traffic go by. It blows my mind. The garbage OH MY GOD. I have never seen so much filth and waste that these people leave behind. We actually moved to a city just outside of Seattle, it is still King county. I moved because I wanted to make sure a tent city wasn’t going to end up in my neighborhood or a foreclosed home turned into a meth lab or worse now RV’s are just parking in any neighborhood and cooking meth. Magnolia neighborhood had to hire their own private security. Honestly I have a good job and I feel like it’s too good to give up to move but I hate Seattle now. I really do.

    • retirebyforty June 25, 2016, 11:23 am

      I haven’t been to Seattle for a few years. I heard it’s getting worse there too. Seattle is more spread out than Portland so I think the concentration is a bit less. For now, the tent cities are close to the downtown area because all the services are there. They are spreading out more, though. Drug is a big problem here too. Sorry, you don’t like Seattle anymore…

  • Sandy June 24, 2016, 6:48 pm

    Agree with all of the comments about Seattle, here for our good jobs, will leave when we retire in 5 years. Getting way too crowded and transit is inadequate. Hoping to be able to sell our house before the market dips again. I think there are still more jobs in Seattle than in Portland.

    • retirebyforty June 25, 2016, 11:24 am

      Seattle has a much better economy than Portland. There are many more big companies and better jobs there. That’s why the Portland real estate boom won’t be sustainable. There are not that many well paying jobs here.

  • Michael June 25, 2016, 2:37 am

    Hey Joe,
    My wife and I will be going on vacation to Portland in September. As the seasoned vet in Portland, anything that is a “can’t miss?”


    • retirebyforty June 25, 2016, 11:30 am

      Salt & Straw ice cream, Rose Garden in Washington Park, Pine Street Market downtown, farmer market, Saturday market.
      Don’t worry about the panhandlers, they are pretty harmless. 🙂 Have fun!

  • Karen B. June 25, 2016, 5:53 am

    Very interesting article and replies. My husband and I are in our late 60’s. We live in Hutchinson, Kansas (about 40 min from Wichita). We have been anxious to move elsewhere lately, but, don’t know where to. Many people here complain that Hutchinson has not grown in the last 30 years or so. We maintain about 55,000 citizen. The interstate does not pass through here on the way to Wichita, and the growth in Kansas has been mainly along I35. A murder in Hutchinson is more often now, but it still makes the news. Homeless people, I guess we have, but the Salvation Army and a few other groups take care of them I guess. I don’t even hear about that problem in Wichita much. Guess troubled people don’t like our few 100 degrees days in the summer. What I am trying to say, that all of your replies made me realize that Kansas isn’t so bad, and to really evaluate before we do make a move, anywhere. Thanks

    • retirebyforty June 25, 2016, 11:32 am

      You should try renting for a few months before making the move. Many places sound nice, but you won’t know until you’ve lived there for a while. Good luck!

    • bev June 29, 2016, 10:52 am

      Karen…I think you are right. We’re also in our 60’s and think about moving often…retiring in a few years. But when we read about all of these problems in other places, we realize that we are pretty fortunate. We’re in New England, and while it’s certainly not cheap here, and the weather sucks…not always, but enough….I realize that I shouldn’t base my happiness on the weather. We have four beautiful seasons, excellent graduation rates, beautiful farms and no crowding, at least in the rural areas, lots of history, clean air and clean water. And we can always drive and hour to a larger city to get our city fix. Just like Dorothy and Kansas…there’s no place like home and sometimes that’s your own backyard. Bev

  • Smart Money MD June 25, 2016, 8:16 am

    Traffic has been horrible in both Seattle, Portland, Austin, and many other “hip” cities. It’s a shame that the infrastructure hasn’t allowed for growth of more efficient public transportation, but I suppose that these are growing pains. The suburbs are sounding more appealing every day!

  • Frugal Pediatrician June 25, 2016, 12:03 pm

    Born and raised in San Diego and will retire here. It’s crazy how many folks from the Midwest and LA have moved down here. I remember when we were more like a sleepy town too. It’s wonderful but the traffic is getting bad. Thank goodness I have a reverse commute and we bought property when real estate had tanked. It’s too hard to move when friends and family are here despite costs if living.

    • retirebyforty June 25, 2016, 4:39 pm

      San Diego was very busy when we went down a few years ago. It’s nice, but still way too many people for me. Way busier than Portland.

  • Matt June 25, 2016, 11:25 pm

    Nice article – I also live in Portland and went to school (as well as grew up in) Santa Barbara. I followed you to Portland a while after you moved here, but I love it – despite the problems you accurately identify.

    • retirebyforty June 27, 2016, 9:55 am

      It’s a huge change from SB to Portland. 🙂 I still love it here in Portland and I don’t know where we could move to. SB is nice, but it’s too expensive. Other locations in CA are just too busy.

  • jim June 27, 2016, 4:55 pm

    I don’t believe the homeless rate in Portland is any different than other major west coast cities. Seattle also has a big problem. So does LA, Hawaii, etc. NYC is significantly higher. Portland is pretty progressive and accommodating and relatively lax on laws enforcing homeless camps and that (I think) makes it more visible and appear worse. In other words: In many cities the police would just run those homeless people out of the visible parts of town and you just wouldn’t see them.

    • retirebyforty June 29, 2016, 7:41 am

      Seems like it is getting worse. I have heard the same thing from people in my area. I think it is more visible in Portland because our downtown is so compact. LA is a lot more spread out. The police should shove the homeless out of downtown during the tourist season. Tourists are getting bad impressions and complaints are up. I don’t care about aggressive panhandling, but a lot of people are put off by it.

  • Jen June 27, 2016, 10:07 pm

    We are visiting Portland for 8 months. We have traveled all over the US for the last five years as we work remotely. We are originally from Florida where the crime is way over the top. We can’t believe the low crime here. It is like a dream compared to Florida. Check out the local news in Orlando, FL for a quick glimpse into real FL living. We did notice that the Portland area has lot of trash everywhere where Florida is very clean. It seems like governmental services here may be lacking. Portland has trees, pretty neighborhoods, nice people and amazing food. After crossing the US multiple times and visiting over 300 cities/towns this is so far the nicest all around city we have found. We are heading to Vancouver, BC for a stay after Portland – that also looks promising. We will see. Thanks for all of your informative posts – very helpful!!

    • retirebyforty June 29, 2016, 7:45 am

      I’m glad Portland doesn’t have a lot of violent crime. We have a lot of property crime, though.
      Portland is still really nice.
      Sounds like a great trip. Enjoy!

  • GV June 30, 2016, 12:14 pm

    Joe I can definitely identify with this article as I live in New York. I live in the suburbs of Long Island so homelessness is not visible, but I commute everyday to Manhattan where being homeless is like a full-time job. Each homeless person has a “backstory” if you will. There is the veteran claiming to have served in some war. There is the individual who is in a wheelchair and wishes to illicit sympathy for their disability. There are those who have dogs with them with cute little faces to illicit sympathy from animal lovers. Then there is the random woman who will claim to be pregnant and have a sonogram picture attached to her cardboard sign. You cannot take more than 3 steps without being bombarded with a homeless person asking for money in some way or another. The streets are filthy and people just lie there in makeshift cardboard homes. We have a pretty liberal mayor in NYC and he has instructed the cops not to do anything. Most of these individuals are drug addicts looking to get their next fix or drifters who live off the kindness and generosity of others. It’s very sad because there are definitely a lot of legitimate homeless people in NYC but those are the ones that are living in the subway or rummaging for food in the trash. Those are the ones that don’t ask for money and need it the most. The ones panhandling are usually con artists. It is not out of the ordinary to see them with a cellphone or wearing expensive Nike sneakers and yet they have no shame in asking for money. Since NYC is a big tourist destination, they know that foreigners will give money. I don’t have the answers either for how to solve this problem but I hope things get better for you guys in Portland. It’s such a beautiful city!

    • retirebyforty June 30, 2016, 3:19 pm

      The “pregnant” women are the worst. They should know better than to get pregnant in that situation or they are just lying. Either way, I don’t give them cash. One of our friends just moved back to NYC. She’s coming back for the summer so I’ll get a full report.

  • james July 2, 2016, 5:23 pm

    I can relate about over crowding and traffic jams. I live in Manila. In the late 90’s traffic was bad but manageable. Population and traffic jams progressively worsened. Now 20 years later the rush hour traffic is a nightmare in hell. I drive 2 to 3 hours in rush hour gridlocks. I get very stressed out and very emotional in traffic jams. Sometimes I feel rage and sometimes I just cry in my car out of frustration. What kind of life is this in the city? Can’t I have a short and relaxed drive back home after a hard day’s work?

  • Josh Crites July 6, 2016, 7:25 pm

    It is the same up here in Seattle. I live in Queen Anne and the city is moving up the hill pretty quickly. I work for the housing authority and we try to provide affordable housing to as many as possible but the need outweighs the supply. Enjoyed the article.

  • Robert Harden September 3, 2016, 11:17 am

    Traffic is getting SO bad. We need wider roads (I5 / 217 / 205). The city is growing way to fast and something needs to be done with the roads. Great article, you hit the nail on the head.

    • retirebyforty September 5, 2016, 9:03 am

      The city planners keep arguing that wider roads won’t help. I think we need more ring roads so people don’t have to go through town if they’re just passing through. I5 is crazy.

  • Terry Pratt April 14, 2017, 12:26 am

    Over and for the past nine years, I have lived sequentially in three overcrowded houses. While it seems as if vast attention and resources are being directed toward the homeless, I see nothing being done people living in overcrowded housing.

    • retirebyforty April 14, 2017, 8:32 am

      How overcrowded were your homes? 3-4 people per room? Just curious. We have 4 people in a 2 bedroom condo. It’s a little tight, but not too bad.

  • Lily @ The Frugal Gene October 23, 2017, 10:13 am

    I should write something like this with Seattle but I haven’t been here long enough yet. I didn’t know the graduation is so dismal – anything under 70% is hard to picture because high school is indeed super easy. Oooh wait… I just realize my friend from Salem was a drop out and he said most his friends did too. That was back in the 90s tho. It wasn’t smarts or the system, it was family problems for them all in some form or another.

    I’m pretty sure (like a 10001% sure) RB40 Jr will be fine and will graduate lol! If not top of his class someday too. Your fears are unfounded, look at who his parents are hahaha, silly 🙂

Leave a Comment