Tpl, exactly it would make no sense to leave from San Jose unless that was part of his original plan. I do hope he decides to stay in Monterey though instead of Salinas. Really the only tourist draw that I can think of in Salinas is the Steinbeck Center, which is a great place to check out if you're a fan of Steinbeck. I just hope all the argueing over whether or not to spend a night in San Jose doesn't scare him off from California altogether!
Maggie, yes the drive Yosemite can be quite a challenge. It's even worse from Santa Cruz because you have to go over Hecker Pass as well. I found though that highway 140 isn't as bad as the other routes (at least to me) because you aren't as high up and the scenery along the Merced river is so beautiful.