This in an interesting exercise, JF. I gather you want to play two different courses on ONE trip; so within two hours of the same major airport.
Well... conveniently for you, San Jose Norm Mineta International Airport is within two hours drive from a lot of things. Unfortunately all the great ones are more than $100, and are tough to get tee times on... I could cheat and say "get a member to take you to Pasatiempo", in which case it would be $60 and teetimes aren't an issue, but the knowing a member part is more than can be expected.
SO... I'd recommend....
1. Fort Ord Bayonet. It's been discussed many times on here - it's a shell of what it used to be, but it still is a very tough challenge for the low 'capper - just put him back at the gold tees and he'll suffer as much as he wants to. Put the higher capper up a few blocks, and he'll make enough pars to keep him happy. It's no marvel of architecture, but it is very interesting, kept in fantastic condition, and it's always under $100. Tee times aren't that tough ever also. It's about 45-60 minutes from SJC, depending on traffic.
http://www.bayonetblackhorse.com/You could just stay there and play the Blackhorse course there also - it is great fun, weird, quirky, tough - but hey, we want diversity... so....
2. I'd say Pacific Grove Muni, as it is the bang for your buck capital of golf... but getting a tee time there is like pulling teeth... so that's out... so for #2 we head you east a bit, and hope you can drive fast. STEVINSON RANCH is NorCal's answer to Rustic Canyon. Wonderful minimalist design, cheap, no problem ever getting a tee time because it's in the middle of nowhere. I've made it in two hours though, so it counts.
http://www.stevinsonranch.com/There, that's decent enough.
TH