When Can I Retire to Portlandia

I have been watching the series Portlandia (watch the video above) which satirizes people my age living the dream of the 1990s of working less, doing more weird stuff, and generally just hangin'. It has gotten me thinking as I take a break from working on a grant application that if it goes well will give me more work, why aren't there more people moving to Portland the city where young people go to retire (as Portlandia quips). A paper by Angus Deaton and Daniel Kahneman show that after about $75,000 a year extra money doesn't make you happier, but it makes you feel you have a better life. So perhaps I'm working to feel better about my life? At the Portlandia end of the spectrum people work a few odd jobs to maintain a minimum level of consumption. I have heard from friends of ours that move to Portland, that these part time barista, bike mechanic, and bar tender jobs are getting harder to find. Our friend said finding a full time job wasn't as hard since fewer people wanted them. Of course this is all anecdotal, but what do expect from a post about Portlandia?