Thank you for the kind words, Ben!
Earning money by rolling above the target is an important mechanic because it incentivises the player to reroll for a higher amount (and higher payout) even when they've already rolled enough to meet the round target. There is a risk then, of course, of rolling lower than your current roll and missing the target entirely, so it is a calculated gamble on the player's part. This is where the "midnight staircase" part of the jam's theme comes in. Does the player keep rolling to attempt scoring higher, or "get off" with their current roll?
If I continue working on this post-jam (which is likely), I think I'll change this to align with feedback you and other people have provided, because it does just break completely once you get enough dice and the game becomes impossible to lose.