Op,
Lots of good advise from people who live in the area, The wife and I live in Silicon Valley back in the 80's and 90's before it got really nuts. However housing costs were going up faster than pay raises during that time as well. So it is always harder do get into a house once you are renting since it hard to save, all the costs in the SF area are higher. If you feel you need to do it, keep this in mind since it was what we did.
Your main housing choose will be, live close to work (short commute), have smaller place, pay higher rent or mortgage and most likely have little spend money at the end of day. If you have any ambition you can always make more money. The other option, bigger place, more of yard, lower rent/mortgage/ long commute extra cash in your pocket, but no play time to spend the money since you spend so much time commuting.
The wife and I chose the short commute since you can always make more money, but you can not make more time. Lots of people we knew choose the bigger place and long commute, then realize their lives sucked and they were stuck.
We bought in the heart of the Silicon Valley, a small townhouse, We borrow money from our parents and I sold stock options to get the down payment. Our commute was 20 minutes to work, but we lived less than 10 miles from work and we drove mostly highway to give you and idea and today it is 10x as worse from what I have been told and the last time I was out there about 5 yrs ago.
Also here is the downside of how nice it is to live in SF and the bay area.
http://sanfrancisco.cbslocal.com/201...-union-square/
https://www.sfchronicle.com/bayarea/...ver-Oakland-86
I can tell you, back in the 80's they had a homeless problem, I grew up on the east coast and spent time in cities like, Pittsburgh, Philly and NYC, there were homeless but most were bums. To the wife's and my surprise, homeless in the Bay area were entire families, can not tell you how many times we saw a family with kids huddle up in a entryway of a build in SF. Very sad and from what I have been reading lately it is way worse now. Just something to consider.
Also, over the last 10 yrs California lost 600K of people moving out of the state and I read that SF lost 29K just in the last year. People do not seem to be moving in anymore.