Really cool idea - this solves a business model innovation problem for dealerships as well. I love the idea of being able to try for weekend BEFORE I buy or lease. Good luck with this - as a UX person I'd be happy to provide feedback on the app and service design.
Fog is worse than where? I work in SSF as well... A) its where businesses like Stripe should be in the coming years (it wont be creative, it'll be internet infrastructure) B) there is a ferry to Oakland (to help alleviate the absurd traffic jams over the bay bridge) and C) bring some variety (right now SSF is all pharma and med device) into SSF.
There is no reason why SSF couldn't be a thriving, cool place to live and work. It takes companies like Stripe to take the lead and have a vision.
Right now downtown SSF is totally boring but add a good grocery store (ahem, Berkeley Bowl) a couple cool coffee shops, wine bars and great restaurants and it would be a perfect fine place to live and work - half way between the south bay and SF.
Buy, renovate or build a place or open a restaurant in SSF now while you have than chance. It will be corporate, funky but potentially cool in 5 years with your creative and financial energy in it.