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In asylum there is the woman who will have you pay 2000 money for 15 minutes with her. I spammed through dialogue after that was done, and it pulled a further 2000 from me and it put me in the negatives.

That's actually a glitch then. She is suppose to take money only when player has some.

If you are on PC, you should go to (Your User)\AppData\LocalLow\LAGS\RingManSpiritHunt and modify your money in the SaveData.txt file.

Just modify the one that says "Money":, not the other one that says "mMoney:", idk what the latter does.

Oh, also the appdata folder is usually invisible by default, if you can't found it, google how to "show hidden files".