I live in San Diego, so it might be just a clash of cultures. But I honesty would like to know, why does the tech community find SF so appealing. Is it just a function of that's were all the VC money is? Or am I missing something?
At the risk of being a bit flippant, it's not that people find SF so appealing, but that they find everywhere closer to work unbearable. By any measure I can think of SF is a deeply dysfunctional city with incredible failures in basic quality of life - but it is the only city around that even begins to offer a lifestyle that many people want.
And frankly, there are parts of SF that I personally would find difficult to live in without a car (or at least bicycle), because they're far from effective public transit or commercial areas. BART and CalTrain don't serve the western part of SF at all, and muni is often slower than walking.
The south and east bay may not have the same density as San Francisco, but then again, it's far from clear that super-high density is a good idea in a seismically active zone. A lot of people seem to treat the choice as being between super-low density and super-high density. The alternative, medium density, never seems to get much P.R., but it seems like by far the best choice.
I think a reasonable case could be made that Champaign Illinois (which hosts UIUC) is more of an urban area than those two cities. At the very least, I think it's better than San Mateo.
I agree that San Francisco sucks (and I lived in SOMA and in Noe Valley, both of which have relatively good [for the area] transit), but it is at least an actual city.
The obvious elephant in the room here is San Jose, and it's telling that you didn't mention it, opting instead to pretend that San Mateo was a "dense urban area". San Jose is an urban center. But it's miserable; nobody talks about moving there. The fact is that San Mateo sounds plausible because of its proximity to San Francisco.
† For Palo Alto, I mean University; you don't need to point out that El Camino runs through it, I know where to go to find the strip malls. :)
Palo Alto is a horrible example IMHO. All of the good stuff is on University Ave and maybe California, the rest of it is just residential and not within walking distance. If you don't live close to University, you definitely need a car.
- It's a relatively big city with more cultural institutions than other areas around the Bay. You can expect many live music shows, plays, and events on any given night so there's always something to do.
- It's a young city with not a lot of kids in most parts of the city. There's a vibrant bar/nightlife scene and you can get around with public transit easily so DUIs are not an issue.
- The food is ridiculous - there's delicious food EVERYWHERE. Cheap delicious food, Michelin starred delicious food, etc. San Diego has some good restaurants but SF just blows it out of the water.
- It's a beautiful city (sans some shitty parts of downtown). I don't get bored of looking at the bridge from Crissy Field or seeing sailboats on the bay with Alcatraz in the distance.
- Awesome access to the great outdoors - San Diego has great coastal access and some decent forests/desert areas east but consider that just across the bridge is Marin county with hundreds of trails of hiking, biking, etc. all within minutes of San Francisco not counting what's in the city itself.
A lot of people do it every day, but I decided it was too much and moved to the Valley. If it weren't for the commute, though, I'd love to live there again.