I don't think that OAK is a better airport than SFO.

At OAK, WN has its own terminal, thus upping the "Clampett factor" as you put it. The array of shops/restaurants/etc at OAK is less impressive than SFO, and the ceiling seems to be lower and the terminal gets less light/has fewer windows than SFO.

BART will get you to OAK, but it will be a BART & bus, unlike SFO where BART drops you at the international terminal. The bus from BART to OAK is about 10 minutes, depending on traffic.

OAK is much closer to my apartment, and a week ago, I was able to leave my place, walk the half mile to BART, train, bus, go through security and be at the gate in 45 minutes flat. But it still felt like I was in a 2nd tier airport.

If you want a good airport experience, SFO would be my choice. Plus, you said you'd have a first class seat. Even with a 60 minute flight, it's still nice.