Hi CM,
I'm on the marketing team here at Trulia, but also happen to have been renting in San Fran for about four years now. If it's just the two of you and you're looking for 1500 sqft. (pretty large by SF standards) but still want to live in a fun area, I'd recommend three areas:
1) Marina: An easy place to live, this area is known for yuppies in their 20s w/ no kids, usually a dog, and has an active (if somewhat homogeneous) bar and restaurant scene. Places tend to fit the exact description you're looking for.
2) Mission: More funky, street-style but a growing area and probably closer to the lower end of your range. There are some great lofts here as well if you're open-minded about living in an edgier neighborhood
3) SOMA: Great loft space as well and you can probably get a new or nearly new unit (unlike the Marina), great restaurants too and probably more the city feel you're used to in Chicago.
You can check out more details and more (median incomes etc.) on the neighborhood guides pages right here on Trulia -
http://www.trulia.com/real_estate/San_Francisco-California/
Good luck - keep us posted on how that hunt goes.
- Tue Mar 25 2008, 16:29