Commentary from a gameplay perspective:
Cory, you've put cool stuff out now that I think you can stand some constructive criticism here: sometimes the randomness in a game can be a bad thing. The original incarnation of Drop the Bomb was a total press your luck game, and so who cares who random it was. But here, to use Joker's Wild references, your balance between Knowledge and Lady Luck is off.
Point 1: Questions range anywhere from $100 to $1000. When it takes $5,000 to win, the idea that I'm answering questions at a 50 questions to win rate is a little unfair (and I spun $100 enough to make that a concern). I know you can't really change the upper value now since you've got a medal that relies on it (first medal I won), but you should consider raising the lower value slightly.
Point 2: Chris's concern about the bomb is absolutely reasonable. I have also spun bombs twice in a row -- once in a 4 question contract, and then in a 5. The idea of, "well, you survived 9 bomb questions and now have a score of $0" kinda sucks. You're already penalizing them by making them answer a "game over" question. Doing 5 of them for no money is over the top. A more fair way to handle this would have be that normal contracts run from 2-5 questions, and then any 1 question contract is a bomb (and since bombs would appear in the center window, the bomb question could still be worth money). So while bombs would appear more often, the individual bombs would be less dangerous.
Point 3: Please don't allow the same thing to appear in a window twice in a row. In addition to preventing a too-easy or too-hard game, it improves the curve on how long a given won game takes. A playtime that is too erratic (in either direction) can psychologically turn people off.
