I hope it works out for your son. I’m sure you know that Bay Area housing prices are distorted by several things that are not driven by free markets. First, so much of our land is off-limits to construction by government fiat and there is simply no more land for building in Silicon Valley. Scarce land means high land prices — unless you are willing to commute 90 minutes to your job from Hollister or maybe 45 minutes from Morgan Hill. House prices are roughly inversely related to commute time to the jobs in the valley. If you value time with your family, you have to pay these prices.
Second, California and federal environmental policies have made the cost of building materials soar. Concrete, copper, lumber - you name it and it is scarce and very costly here, much more so than in other parts of the country.
I bought my first house in 1978 in Palo Alto for $100k and my Dad said I was absolutely nuts, too. Dad had the perspective of living in Missouri and Pennsylvania where land was plentiful and you could simply move further out from the center city to get a cheap house in a new subdivision. You can’t do that here. I was scared to death making that first purchase, but I had arrived in 1973 and the same house was going for about $50k at that time. I missed the huge run-up in prices in the early 70s, so I jumped in and (luckily) things worked out for me. Of course, I had demographics and the (somewhat) early blossoming of Silicon Valley working in my favor.
Today, even though California has the worst business environment in the country, we do have a few notable exceptions such as Facebook, LinkedIn, the new Apple campus, Google, etc. all within spitting distance of Cupertino. There are still fortunes to be made here in tech. Best of luck to your son.
I bought my first house in Campbell in 1972. Although I left the valley in 1973, I kept the house and rented it out. I eventually sold it a few years later and made out like a bandit.