I may be biased since I lived in San Jose for a while, but definitely San Jose. Palo Alto sometimes has that small college town thing where everywhere can be unexpectedly busy (like why is a sit down restaurant bar absolutely packed with 22 year olds doing shots? Because the college bars are too full to even enter). San Jose is a little dull, but charming. I’m thinking northside, like around backesto park. Palo Alto’s proximity to both SF and all that state park/open space preserve to the west is really nice, and I think it might stay a bit cooler than San Jose, which occasionally gets toasty, but still, I’d pick SJ.