I feel the same way as all of you guys do about Chicago. You definitely get a lot more real city than you do for your money there compared to Portland. Transit is better / more substantial, better cultural institutions, and it's way cheaper. I guess the food scene isn't as good but I can't imagine it being bad either.
After living in London and visiting other world cities and big US cities I feel like I'm overpaying to be in a lower tier US city sometimes. My rent in London was about the same as I pay here, granted the space was smaller and not as nice, but in exchange I had access to some of the best transit, museums, restaurants, shopping, parks etc. in the world. As I've traveled more I've also realized a lot of the things that Portland is known for are not unique to Portland. The good coffee shops and bike friendly culture can be had in Berlin for less and it's often times it's done better. DC and Minneapolis seem to be making better strides with bike infrastructure investment and Denver is putting a lot of money into transit. Yet we're having some of the most insane price increases. It doesn't make sense to me as to why it's happening. It's great here but not *that* great, and certainly not great enough to justify some of these prices.
I live in a new building and a huge % of the people moved here blindly from other states. Primarily California but there's plenty of east coast or even PNW transplants in the building. Many of whom are using their savings to be here and are still looking for jobs. It will be interesting to see how it pans out when a lot of these people can't find jobs here to sustain the high rent.
One couple from Chicago visited Portland for a few days and decided to move here for the "culture and to live in a city where they could live without a car". Two months later I see they bought a Subaru. Talked to one of them in the elevator recently and they said they don't really like it here because the people are strange. I wonder how many transplants will end up leaving for reasons similar.
Overall my biggest concern is that there is a huge disconnect between the prices in the housing market (rental and owned) and the local wages and job market. It's also worrisome that it's rare to find any property for sale under $350,000 in inner SE and NE and N. Developers really should start building condos again. With interest rates right now, my mortgage would definitely be lower than my rent right now. The only problem is there's not enough supply for people like me to find anything in the areas I'd want to live. The only two condos I can think of near me (28th & Burnside, and Division & 26th) only have one unit for sale in each and they're over priced and have weird layouts... So in the mean time way too much of my monthly income will continue going towards rent.