I feel like at a certain point the game is just not winnable anymore, because the second game (at least for me) always asked for lower and it wasn't physically possible to get the arrow under the bar. And I couldn't take a single loss to raise the bar to acceptable levels because it cost me my entire cash on top of the 1k you are allowed to go into the negative.
That aside, I really like the idea and the way you made a failed playthrough loop right to the beginning of the next one is awesome. I see a lot of potential and would love it if you would continue working on this project, it is really promising!