Well first of all, everyone's home in the bay area has doubled in price in the last 5 years... that's just how the market has bounced back since 2007. My parents place in the east bay dropped from it's grossly inflated price of probably over 500k to maybe 150k in about 8 months, only to recover back to where it should be hovering around 400k. That's just how things have gone.
I've never had a good vibe from shallow alto. I'm a bigger fan of denser areas with more culture. I've always felt like Palo Alto and the entire south bay was a bit devoid of that. Too much suburban tract style city planning. with too much try-hard copy cat commercial development. It's the same critic I have for a lot of areas in the east bay as well - including where I grew up.
Additionally, on the Peninsula, you don't have Bart. As somebody who swears by the need for accessible and reliable public transportation, I just don't feel like the peninsula south of the Airport really does much in the way of that. Caltrain doesn't run often enough, nor is it very efficient, and the bus systems in the area, are from what I understand - horrible. That's part of why 101 and 280 are constant shitshows, not only do they connect two of the biggest cities in the country, but they also lack proper public transportation to take the load off the freeways. San Mateo and Santa Clara counties still refuse to add on the Bart tax to join the rest of the area out of some sort of idiotic spite, so I'll pass on the hour+ commute in stop&go.
On top of that, the capital you need to accrue in order to get into the market on the peninsula is outstanding... the median home value for a place in Menlo or Palo alto is like 2.5 million bucks! anywhere else on the peninsula is at least 1.5mil. It's far easier to get into the market in the east bay or even north bay without having to risk just about everything - even if you're well off. Why get a place on the peninsula requiring you to commute seemingly forever with a stupid high mortgage rate, when you can get a place almost anywhere else in the bay area for way less? I'd rather live in San Carlos any day over Palo Alto.. and for half the price of even that I could get just as cool of a house in Albany or El Cerrito. For half of that I could just Bart in from Concord or even parts of Walnut Creek. If you can afford a 2.5 million dollar home, why not just invest in the east bay anyway - get like 3 homes for the same price, rent two of them, and let them all pay themselves off while you work half as much and ski even more. Winner.
It's one thing if your job is in Redwood City or San Jose (In which case still, fuck the peninsula, and live in Los Gatos or Alamitos so you have reverse traffic and live in a nicer community and you're closer to Santa Cruz) It's another if you work in SF anyway. I'd take bart or even a fuckin ferry from the East or North Bay into the city with my bike any day over the stress of having to find parking or pay some stupid amount just so I can sit in traffic nuking the atmosphere listening to KCBS tell me for the 7th time that I'm going to be stuck behind 101 traffic because another jackass caused an accident on the Dumbarton by texting their coworker about how the beta isn't working on the new app project. Meanwhile 82 and 280 are a fuckshitstack as per usual anyway, so you'll be late for your tinder date tonight. That's the life of a 20 something enduring life on the peninsula. I'll pass, and live wayy closer to skiing for much cheaper.
