Dumb question from an out-of-towner: Does it make sense to stay in a hotel somewhere in the Mountain View / Sunnyvale / Cupertino area and use Uber to get around? I'm not a fan of bay area traffic, so I'd prefer to Caltrain from the airport to a hotel and use Uber after that if it's feasible.
It's on a Saturday, so traffic shouldn't be a big deal. Prices in SF and South Bay (MV/Sunnyvale/Cupertino) tend to be similar. So it's really up to you. But SF does have a lot of options for budget hostels (outside of the hackerhomes that are available on AirBnB). If you have the cash, I would rather spend it on a nice place in South Bay then on Uber.
(information in case you drive, or are wary of your uber driver making you sit in traffic)
Saturday traffic is not bad (though all things being equal, 101 will always be a bit iffy).
Friday rush hour will be relevant since the reception (if you are going) is from 7pm at the YC office. FYI try to avoid 85 south between 101 and 280, 101 entirely, and 280 south after 85 or thereabouts.