I tried NOLA for a few weeks in my 20s - loved it, got a job bussing tables at Brennans, moved into a house with some musicians, lost all $4k of my savings drinking and gambling, and called my sister for money to take a greyhound home. I really dig that town, and Portland blows, but I think it's one of the places I'd probably lose my shit in. Some places are just too easy to stay out all night in.. and have a kind of depressing spiral for a habitual drinker/gambler/sex addict. Vegas, Prague, and NOLA are the three that I can think of where I go to the dark places, go broke and get suicidal. Also, not ironically, my favorite places in the world. But I learned that I need to have a ticket out.