Well, that's part of the question... I think one of my leaks is that I have been racing on the bubble as only a slight favorite and after losing the coinflip I'm caught as the short stack and barring catching cards I'm OTM.

I'd definitely do a S&G on a raggy flop. Most likely on a board with high cards but no A. Most likely not on an ace high flop, since that's the button's most likely holding.

Ideally, the goal is to get the Button to fold more hands. If I raise all-in preflop the Button will call, but possibly he'd fold on the flop if he missed...