Where should I live in the SF Bay Peninsula?

[goofyballer]

In June I graduated college, and on August 6th I begin my new career as a software programmer in Redwood City, CA. The one problem is that I don't have anywhere to live yet. I get a $2k moving allowance as part of my contract, so my plan when I get back from Europe on Tuesday is to use that allowance to move into a hotel for a week or two while I search for apartments in the area.

Anyway, I know we have some experts on the Bay Area here so I figured this would be a good place to ask what a good city/neighborhood would be for someone with my lifestyle. Relevant factors:
- Based on salary + a conservative estimate on poker winnings, I expect to make $70,000 to $100,000 per year after taxes. I have no idea how much that means I should be spending on rent per month.
- My office is 3 miles from the Redwood City Caltrain station; sadly I think this eliminates the option of living in SF itself and taking the train to work. I really, really don't want to spend 2 hours in a car every day, and I expect to be driving to work, so being in a location suitable for a shorter commute is important to me. The office is off of 101 at the Woodside Road exit.
- Ideally, I'd like to be near some nightlife where I might find people my age (22), or at least not that much older. I do plan on going into SF a lot, as I have friends there and am planning on getting season tickets for the Giants, so if I just have to go into SF for that whole bit I can deal. However, my friends have said that SF nightlife tends to be older people (like, late 20s plus) because of how expensive it is.
- I don't want a roommate at this point. This may change in the future if I meet someone I think I'd have a fantastic time living with, but I want to enjoy being a young professional and don't want to roll the dice moving in with someone I don't know very well.

I grew up in Marin so I'm not really that familiar with the other side of the City; so, thanks in advance for any advice you guys can give me.