So I'm thinking of moving to Portland...good idea or bad idea?

I've spent most of my 20's stuck in a small city in Florida that makes me miserable -- minimal job prospects despite having a double B.A. in English and History, sky-high housing/rent prices, limited dating pool (seems like everyone who has a lot in common with me is either taken or not interested) and honestly, I'm sick of searing heat and humidity every damn summer. I'd have bailed a couple years ago if it wasn't for a few financial setbacks. (Nothing like having to pay $1000 - $1050 in rent by yourself for five months in a two-year period to eat up your savings...)

I'm currently trying to learn Arabic in preparation for a Master's Degree in Middle Eastern Studies. I can't get it from any of the local universities, and the closest major city only offers it to a second-year level. I'm currently taking first-year courses online. Portland State offers 3 years of Arabic and I could also pick up a bit of Farsi/Persian. (Admittedly, I'd have to establish residency and not take courses for a year, or hemorrhage money for non-resident tuition.) I want a day job that doesn't make me hate myself (currently I'm working customer service and loathing it) while I study.

The thing is, I've heard that Portland's starting to develop the same socio-economic problems as my current city -- minimal job prospects, rising housing/rent prices, etc...

I like the idea of living in an eco-friendly city with a strong counter-cultural movement, a ton of craft beer, more girls (or the occasional bottom) who might like me, and lots of grey skies & rain...but I also have three ferrets to feed, bills to pay, and the clock's ticking. I turn 28 in a couple of months, and I'm sick of being miserable. I don't want to move and then be miserable AGAIN, and jobless for an indefinite period to boot. (I can do my current job remotely, but my department manager hates me because I sided with someone who was sexually harassed by one of her cronies, so I get the feeling that I'm not going to be offered the opportunity to work remotely like other people who've moved.)

So I'd like your honest opinion...should I pack up and make for Portland in a couple of months, or should I find somewhere else to move to? (I was also considering Seattle, but that's going to be a separate post in the Washington forum.)