I understand your thinking Prospect, but I still like a bet of less than $55 here.
(Why not $55 to cover a natural? It opens you up to being in a tie if he wins all-in while you lose $55. I'll take my chances on his blackjack instead of opening that door. Better yet, bet $52.50 or $51 if the rules allow it.)
As others have noted, you're in a great spot. You'll get last bet on the final hand, and it is quite likely that the game may not last that long. When in this position, I think it's pointless to risk a swing on this hand trying to create an even stronger situation. Wait until the players prove they are a threat by winning this hand. It's worth noting that players 1 and 2 still have less than half your bank even if they win this hand.
The decision would be slightly more difficult if there were only two hands left. Then the ability of player 3 to take the high on the final hand is more dangerous. But here, with an extra hand to go, you'll be able to bet behind player 3 on the last hand, and even if he has the lead you're not in bad shape, because you're guaranteed either high or low behind him. Ideally, you'll get low and double-down high with Curt's revenge.
I'd like to compare the numbers here on a large vs small bet on H-3, but I'm out of time today. Basically, you're weighing the risk of a swing against the reward of having more than a half-bet lead if you both win the hand. Intuitively, I favor the small bet. I hope my intuition is backed up by the numbers.
I'll try to revisit this over the next day or two, and post some numbers. However, I'm departing for a vacation in the morning.
