Grew up in the area, left in the 90’s but still visit regularly. I actually think the OP has many valid gripes, if overly whiny in delivery. Portland is a wonderful city with many great qualities, but if you aren’t amenable to its many annoyances (per the OP) then it is much like being nibbled to death by the cuts of a thousand misplaced poorly-implemented good intentions. For example, yes, they really do indeed think that a person peeing in an open reservoir (that foliage, bugs, gees, ducks, and polluted rain fall into constantly), necessitates wasting millions of gallons of fresh water because…umm…“ick”?
Some added comments:
The girls/fashion. If you don’t like the body-mod tattoo tattered shlumpy vitamin-deficient look, then yes the rest of American cities will look like supermodels in comparison. Also, for as healthy/enviro/vegan as Portland lauds itself, every-frickin-body smokes here. It’s like visiting Italy.
The transit is indeed overhyped. Expensive and too compact, it serves the core district, but not the region. It is great as a test case to show that you can indeed build new transit into a complex old city plan (bridges and rivers and hills, oh my!), but it is a half-assed implementation that didn’t really solve anything.
The economy seems healthy and thriving, but really only from a subsistence/service perspective. Portland is still an industry/service/port city but not generating its own tech or culture to make it sustain the Wall Street, Saks 5th, Silcon Valley yuppie segment. IMO, this is a good thing and part of its charm, but good luck finding a high-salary career.
“Chinatown” is really just “A block or two of some bilingual signs”. Being a coast port city, it’s strange that Portland is so indistinct in its lack of ethnic city segments compared to San Fran, Seattle, Van BC. For good or bad, ethnicity is much more distributed and integrated, there is no losing yourself in the charms of another ethnic district like other cities can be. It’s all just…Portland.
It is so much better now than it was in the 70s/80s. Unimaginably better. We’re talking South Central LA, NY “Warriors come out to play!” level of decrepit decay shittiness. I’d trade today’s weed-baked petitioners at Whole Foods over bullet holes in my windows any day of the week.