Is the bridge over 101 at Ralston done yet? I have an Oracle Users Group meeting at Oracle next week and was doing a little route planning. Thinking about taking Caltrain to San Carlos and cutting over 101 at Holly instead of going up to Belmont.
I know this answer is too late, but my office is near there & I've tried all the nearby CalTrain stops: Redwood, San Carlos, Belmont, and Hillsdale. I regularly mix them up for my morning commute (then ride all the way back to Santa Clara in the evening)
If you don't mind a 15-20 minute ride, you can cross on the car-sheltered pathway at Hillsdale and then take a footbridge from Foster City across to Redwood Shores, directly behind Oracle.
Likewise, you can cross at Whipple and take the bayfront no-cars path from Redwood City up to Redwood shore, alongside the San Carlos airport, for about the same time investment.
Personally, I don't find Ralston or Holly to be particularly intimidating bridges for crossing 101. Ralston is easier imo, both have marked bike paths.