I would highly reccomend Burlingame personally, short Caltrain ride to the city or to PA, cute downtown, good restuarants and bars, great weather & more reasonable rental prices than the city. Oh and since ive moved here my convertible has not been broken into *knock on wood*

Unfortunately, nowhere on the Peninsula or South Bay is not suburbia--nothing has anything resembling the energy of San Francisco or Oakland.

San Mateo is sort of the Big Town on the Peninsula, with bars and such; I find it kind of sterile, myself. I like Redwood City: it's got just about all the stuff I need, and it's the most Oaklandish of the things outside Oakland. It lacks pretense, and it's just a small little city, with its own artists and freaks and little communities, and doesn't pretend it's anything else (unlike Palo Alto, which seems to think it's highly-cultured and interesting).

If you're not in a hurry, I recommend visiting the towns from Burlingame down to Palo Alto, and watch what happens from 6pm to 10pm on a Saturday night.

It's all suburbia, though. That's the tradeoff of not living in SF/Oakland.

I kinda agree with Chris.
I was reading your list of attributes you're looking for, and I was thinking no sweat...until you got to the SF stylee part.
There simply isn't anywhere on the peninsula where the vibe is like SF. Burlingame and San Mateo have downtowns that are walkable and interesting (for suburbia), but it's not the same. There's a reason why SF is SF, and why it's expensive.
Parking, sunny weather, and not having to worry about your car getting broken into, THAT we have in spades. But the peninsula is the burbs, so you need to
decide if you can really deal with that.
I also agree with Chris about RWC. I've been living here for about a year and a half, on the east side as well as the west side(currently). I lived in Oakland before I moved over here, and I really don't miss the constantly-looking-over my shoulder part.
Redwood City's pretty diverse, cheaper than Shallow Alto/Menlo, and conveniently located. The downtown is booming after a big revitalization effort, including the old Fox Theatre, which is re-opened and bringing live music and something resembling nightlife to the burbs.
I lived in Oakland before I moved over here, and I really don't miss the constantly-looking-over my shoulder part.