I'm kind of the reverse. Went from living in Chicago and commuting within the city out to the Bay Area. I ended up in Mountain View commuting < 10 min. and 1.

I'm kind of the reverse. Went from living in Chicago and commuting within the city out to the Bay Area. I ended up in Mountain View commuting < 10 min. and 1.2mi away via bike or car which was extremely lucky. Now I moved to Redwood City and I'm 30 min. and ~15.5 miles away, but at least I can take 280. I definitely hate the longer commute, doubly so because I have to drive and actively focus vs. be on my phone, read a book, etc. Barring the fact that most of those companies have urban satellite offices, I think I'd probably go to a small suburb with good job opportunities in the surrounding area over a city any day. Every time I drive up to SF, I'm reminded how much of a nightmare city driving/parking are. And I'm also reminded of how insanely safe I feel in the suburbs compared to the city (I'm in one of the nicest parts of RWC so others closer to El Camino/101 might feel differently there).