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Provided I was making enough money to live in either comfortably I would go San Jose. I prefer the city of Boston, which for built environments is one of my favorites, but San Jose has much better weather and closer proximity to other cities and activities I really like, like San Francisco, Oakland, the redwoods, better skiing etc.
Also, San Jose has some pretty cool streetcar suburb style neighborhoods which TBH are my favorite type of neighborhood.
I'm from San Jose, grew up here. Weather aside Boston is a better city then San Jose in every measurable way. San Jose is nothing more then a bloated sleeper community. The true comparison would be Boston to SF or Seattle.
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