Seems to be some sort of goofy money bug going on. I had 75 which was the max for my level, took a cab, bought the dvd and the drill. That left me with 20 bucks. Came home, went into my room and it jumped to 50 bucks. Went to sleep and woke up with 100. Figured cool I'll go buy the pants and come back, it left me with 50 on the dot. Went into the bathroom to steal money for the first time and i walked out with 49 dollars. Apparently I stuffed a bill in moms bra and left. I think I'll just hack the money for now.
Edit - Tried it again except that it pulled 80 bucks out of moms bra and then it takes a dollar away at the end of the text before you walk out. The patreon walkthrough says I should be getting 10 - 25 and so far I've got -1 and 79.