What's the chance the house will be bankrupt by a mega whale after the first bet? 49.5%
After 2 bets? 74.4975%
3 bets? 87.1212375%
4 bets? 93.496224937%
30 bets? 99.999999874%
Since anyone can challenge the house for 100% of it's bankroll at any time, bankruptcy is basically inevitable.
I just read your post. It's very similar to mine.

What you're missing though is that in the rare chance that the house doesn't bust it has made such a massive profit that its expected profit is still positive.
Let's say you played a coin toss game that's weighted 60:40 in your favor, you had $1000, and your opponent had $1000. You can choose how much you wager each toss, and you keep playing until either you or your opponent is bankrupt.
If you bet $1000 on 1 toss, that's basically a 60% you'll end up finishing the game with $2000, and 40% you finish with $0. Only an idiot would play like this (if you happened to only have 40% to win instead (-EV), then this is actually the optimal way to play).
The problem with these investing games is that we don't get to "keep playing until either you or your opponent is bankrupt". We only get to play for as long as the whale wants to play. He might only make a single large bet. What if you're playing the 60:40 coin toss game against an opponent who will call "game over" at some unknown point in the future? Would that change your strategy?