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Personally, I just don't think commuting is worth it if you can avoid it, especially with gas prices as they are (not to mention the stress). Your job is located in and surrounded by suburban type places. I would accept that reality instead of trying trying to have it both ways.
Have you considered living in Fremont? It's the town just north of Milpitas and it has a BART station....so if you want to go to San Francisco on the weekends, you can just hop on the BART train...much less stressful than driving to SF and then looking for a parking spot...and seems to run more frequently than CalTrain (which is the train you'd take from Redwood City).
Also, if you like a more urban environment, San Jose might be a better option than Redwood City. As another poster said, SJ is a far cry from San Francisco, but more interesting than Redwood City. Another possibility might be Mountain View. It has a cute downtown area with cute (non chain) shops and restaurants and some urban type housing...although it does tend to be pricey in an already expensive area. Once again, a far cry from San Francisco, but worth checking out, and a closer commute than Redwood City.
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