i live in San Mateo, i ride to Palo Alto for work, and sometimes i ride to San Jose to hang out w/ the kids...
i seldom take the surface streets anymore cuz of the wacky drivers on the Peninsula,
i'm mostly a Bay Trail guy now. the Bay Trail starts in Millbrae by SFO, and is mostly
continuous all the way to Redwood City, you have to bike along the frontage road at
points, but the Bay Trail actually extends all the way almost to Sunnyvale now.
when i was roadie/mtb'ing alot, i used to take the Alameda de las Pulgas, Canada Road,
and Foothill Expressways alot, but now being mainly fixed, i use the flatter routes
like the Bay Trail, Middlefield, and anything east of El Camino, but i can still knock out most hills.
51 x17, 50 x17, 49 x17 most of my bikes are set-up with these ratios cuz i still occasionally
like the skidtricks too, plus i ride alot of hills exclusively brakeless in SF and need to skid alot.