I wouldn't hesitate to book the OP's proposed itinenary on separate tickets (I'm a bay area native and used to work at OAK). That's plenty of time.

While Southwest doesn't consider any of their airports "hubs", OAK is about as close as it gets. They have a major operation there and there's plenty of flights between SoCal and OAK. If there's no hold luggage the OP can connect airside too.