Yeah, runs don't save when you quit since the game is designed around sub-1 hour runs
Viewing post in Is there no save game?
Been a while so I'm not entirely sure, but I think each hand is compared to the opponent's hands individually and the result is summed. One winning hand and a bust will cancel out (unless you've got a Blackjack bonus)
Also your betting strategy is known as the Martingale, it actually pairs pretty well with the Hero ability since without it it's a bit slow