Boston or Silicon Valley?
SwellJoe: "Is Boston significantly cheaper than SV (I'd probably be in the Mountain View area)? It's hard to find comparable areas for cost of apartments and such."Mountain View is very nearly the same price as San Francisco.  Because of Google it is among the most expensive places in the valley.  I've lived here since we did YC last year, and I've enjoyed it.  It's a lovely, quiet, and highly technology focused area, with good restaurants (as long as you like Asian and Mediterranean food), cool little groceries and produce markets (mostly Asian and Mediterranean, but also the Milk Pail which is close to heaven for fans of fresh food), a fantastic library, and even a decent cultural scene (though it is very much white bread small town culture...the performing arts center is excellent for such a tiny town; the massive tax base of the city insures most city services are excellent).I don't know anything about Boston, but I've heard it's also quite expensive.I'm paying $2145/mo for a two bedroom rental house a few blocks from downtown Mountain View (with a garage).  It's pretty big compared to where most of the folks I know out here are living, but I moved from an even bigger place in Austin, so it was definitely downsizing for me.  I've been shopping for a place in SF, and have found that prices are pretty similar for smaller places--$1600-$2000 for a one bedroom (sometimes plus small office) apartment in a decent location.Salaries in California are enough to make up for most of the higher cost of living, as long as you don't have a strong desire to own your own home anytime soon."- Any advice on which of two hypothetical is better: big fish little pond or little fish big pond? Alternatively, would you rather be at an important team in a lesser-known company, or a less-important team in a well-known company?"How long is a piece of string?  We can't tell you what the best work environment is for you.  You'll need to try it and see.