Actually, if you had gotten into property then, you would be sitting pretty right now. The pricing in Cupertino in 2001 was about 1/3 of what it is right now. Might have been less.
My parent's house is Fremont is worth a ghastly amount of money considering they only paid 15K for it in 1960. They don't care, they just live in it.
High prices have been a reality in the Bay Area for a long time. I remember being aghast at paying 112,500 for this:
https://www.zillow.com/homedetails/3...18339947_zpid/ in 1986. I sold it for 185,000 in 1992. You see what's worth now.
My point is people in the area have always found ways to adapt. My parent's new neighbor is some 30 something who got a 'deal' at 765,000. He's a teacher and his wife is an admin with the school district. Neither is from a rich family, they had a house somewhere else in Fremont that they sold to get into this one. Their mortgage is probably crazy, but so was mine (comparatively speaking) in 1986 if you consider percentage of income. The house will never do a Modesto or Nevada price dump, so they'll be ok if they stay in for the duration.
I don't think the tech bubble will ever completely burst in the Bay Area. There's too many resources and frankly, the types that run those companies don't want to live in North Carolina or Texas.