I agree, making the first tour be from home makes it a lot easier - you don't have to deal with packing the bike & if things go drastically wrong you can get a ride home from a friend.
How about drive to Santa Cruz, ride to Monterrey, camp, then ride home the next day? Moderate distance, enough services, decent views, pretty flat. Or any loop up in the wine country would be nice.
Bicycle OUtfitter in Los Altos is very touring friendly, they might even have a clinic, I think they used to.