Bailey looks more and more stupid and unteachable every week. Every week he climbs for money, gets a broken jaw and crawls away, collecting teeth from the floor. And the next week, after spending on a new bodyguard and paying the dentist well for new teeth, he comes again. And again. And again... Does he like spending money rather than receiving it?..
This annoying quest with Bailey needs to be finalized somehow, in my opinion, at least so that it doesn't look so strange.
1. Add the opportunity to hire a lawyer (It is unlikely to be very expensive, given how openly and dirty Bailey acts) and jail Bailey for extortion. The new head of the orphanage will no longer rob the pupils.
2. For criminals for whom contacting the authorities is not the best idea - the opportunity to hire thugs so that Bailey "accidentally" gets lost in the woods and never comes out again.
3. The opportunity to negotiate with Bailey himself so that he would moderate his ardor and know the measure. Having beaten him twice, on the third offer to stop spending money on bodyguards, agree on a normal amount and do not interfere with each other anymore. A high skill in English/Math/Skulduggery/anything else will additionally bring down the price. Say 350/250 a week or so. At least, the "service" provided in Bailey's orphanage does not cost more, while the price is not very small, but also not very annoying. At the same time, however, you give Bailey your word to pay the agreed amount in the future without frills, and if you break your word, then deeply offended by this fact, he will not stint on teaching you a lesson and taking the maximum from you.
4. Just for lulz, an kind idea in the style of MLP - Bailey robs pupils not out of greed, but because his (her) wife (husband) has cancer, and even the simple maintenance of her (his) life costs a lot of money. For healing, you need some kind of mythical miracle potion or artifact. Having somehow found out about this situation, it can be found, having tried, having received eternal gratitude from Bailey and dramatically improving his character. Of course, with the cessation of any extortion