I can't believe you put Portland and Austin in the same sentence. Nothing wrong with Portland, but Austin is simply in another league: I don't believe there is another place in US with such combination of technology, nightlife and dating scenes. I do feel sorry for all guys in their 20s living in Bay Area.
That's funny - I actually feel sorry for all the guys in their 30s living in SF (and that includes me)! Technology, nightlife, and dating seems pretty great in SF. And when you have no obligations, you can take advantage of all of that.
Most of the programmers I know are now in their 30s with small children. We're trying to figure out how to pay a mortgate and preschool costs that easily exceed $1000/month.
Salaries are high here, and two income families can swing it. But I have realized that high costs are toxic to freedom. Yeah, if you score huge with a startup you'll have enough money be free of the daily grind, but that isn't really in the cards for most of us, even if we take a real crack at it.
I know people who have cashed out of the real estate market in SF and moved to Austin, and they absolutely love it. I think I'd enjoy it there, too. I think that it's probably easier to gain financial independence and start living on your own terms in other cities. And these don't have to be crappy lame places - these are really entertaining places to live. In some ways, I think the cost structure of SF makes it a less entertaining place to be, because people have to make more decisions based on paying the mortgage than doing something creative.
But my wife and I have a huge extended family in SF (parents, grandparents, cousins, nieces, nephews, etc...). I've actually tried to leave, but just I can't do it. And to me, cost is the only problem - if you have the dough, then for a certain type of person, SF may be the most pleasant place to live in the US.
I've lived and started a business in both Austin and Silicon Valley. If you're starting a tech business the valley is a lot better. I miss the weather and the live music scene in Austin, but the tech startup climate is orders of magnitude better in the valley. I'll go back to Austin when I've built the business that I want to build. Until then, I'm staying where the ground is most fertile.
