If you got the "goodboy" ending then you would have gotten some money at the start of the reset. And yes, gym requirements stay the same because your stats carry over. (its based on your current stats)
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Well I got double the money, meaning I carried over my money, but also got the same amount on top of it. But my stats didn't carry over, I started over at groundlevel again. I also found out through reading the save file that my mobility was -979 (shown as 1).
Is the goodboy ending also there where the boss eats Limbo and tells you "Game Over"?
If not, then I guess I found a bug. I could send you save files from just before I entered the Boogie Boss and right after the "reset" happend.