Was raised in the San Jose Area -- However I can't answer any of your questions about the businesses you are looking at - sorry. If you are successful in getting a bike rented then I'd suggest you spend some time on www.pashnit.com -- a California based site that details all of the great roads we have to offer out here.
Locally I can speak to Ca-84 from Fremont across the bay to Woodside and up to Alices Restaurant (Local Motorcycle Nirvana).
The PCH (Pacific Coast Highway) - South from San Francisco (or Alices for that matter) to however far South (or North) you would like to go. The area from San Jose - West to the Coast is rife with great roads and fun twisties there is no lack of ways of getting from the urban city center to some remote country.
End of Feb can be WET and Windy - not always, but you should plan on it. Cool - Not cold (for a Canadian), but cool.
East from San Jose - well there's a GREAT set of roads that will take you over the highest mountain in the area (Mt. Hamilton) and then onto Mines Road, finally onto San Antonio Valley Road and Finally onto Del Puerto Canyon Rd that will dump you out onto the I-5 which you should then take North to the 580 West to the 680 South back into San Jose. There is also the Calaveras Road which will take you out of the little town of Milpitas up into the Eastern Foothills on a scenic tour all of the way into the afore-mentioned Ca-84.