From a visitor’s perspective Portland seems cool and hip. What actually goes wrong when you live there?

While I haven't lived in Portland, when I visited in 2019 I was like, this is a larger Santa Cruz. And I have lived in Santa Cruz so I can make some extrapolations:

* Stifling lack of local prospects; in SC, the majority of jobs were "over the hill" (SJ/SV) making it a bedroom community. Portland has a little more going on for itself but it doesn't have the strong jobs pull of a city like Austin, which Portland has often been compared to in the past.

* Isolated city. If you leave Portland you reach rural farmland relatively quickly compared to larger US metros, which have a cluster of coties SC as noted has some distance to the city, but also proximity to farms east around Watsonville. SC being a college town with a major university contributes to the difference, bringing in a wider young demographic. In both cases this contrast and close proximity enables a dynamic of "city vs country", which exploded in Portland in 2020's protests with aggressive displays and a fatal shooting.

* Ethno-nationalist legacy: Portland was designed to be whites-first and only reversed on that relatively recently. California harbors some of these sentiments, but mostly not as strongly. It adds a layer to the culture that, while not always blatancy obvious, makes it feel more insular.

IMHO, you missed the biggest point: Lack of sunshine. Outside of summer, it's mostly cloudy, coldish, and generally dreary weather.

Portland State is an OK, not great university to boot.

I stayed there a bit and there isn't so much of a single people meeting up type thing. A lot of people stay home, go shopping go home. There was much more of an events happening meet people vibe in NYC.

New Orleans has one of the highest murder rates in the country. It's not a safe place.

You misread - they fled to New Orleans from Portland, they weren't trying to get away from the murder rate.

Besides, NOLA is fine. Murders aren't evenly distributed; there are plenty of perfectly safe spots and lots of safe activities to do.

In 2019 they were at at all time low. I’ll still take it over Portland where people treat me like I don’t exist or as a means to an end.

I’ll take “treat me like I don’t exist” over “make me not exist” any day. ;-)

Barring a car accident a few months ago no one has ever laid a finger on me or made me feel unsafe here.

I visited Portland in late 2020 and I couldn’t believe how dystopian it became. It used to be such an amazing city.