You will spend 8 to 10 hours doing what you could do in 2 hours with your master plan. You will, from time to time, not sleep in the bed you had planned sleeping in from time to time, and that won't be because you got lucky at the hotel bar. WN is the business flyer's friend out here. You can mix/match most city pairs, and there is plenty of frequency. I don't fly them very frequently, but I just suck up the $12 to not worry about check-in time, have 75% of the aisle seats available for my choosing when I walk onboard, don't have to gate check my carry-on because of RJ size (which means I can travel with one bag total).
As a UA Gold in SFO, there will be, at any given time, probably a few thousand people in the airport with higher status than you.
As far as OAK, there's free wifi and plenty of plugs. I get a xbux iced tea and it is just about as good as sitting in a UA lounge, and maybe better, because I don't have to keep running back to the monitors to see the creeping delays and/or cancellations of my flights.