do debt bounty hunters still only show after the maid academy? also how do you get into debt quick
I moved it to be earlier, they can now start appearing after you've been to the dungeon for the first time, which will always be when you meet Gray in chapter 1.
To get into debt quickly in the early game, spend as much money as you can at the market, then wait for rent to be due. Once you're in the negatives, there's a brief grace period before bounty hunters can start showing up. The odds of bounty hunters showing up are based on how long you've been in debt and how much debt you're in.
In the mid-late game, you can talk to Gerard and he can put a "fake bounty" on you whenever you want, so you don't actually need to go into debt anymore to visit the debtors' prison beyond that point. I believe he becomes available in chapter 3 sometime.