Chris doesn’t learn. Not unless it’s a decade long grind teaching him not to fall for randos pretending to be women or an immediate consequence he can connect to the offending action. Which he will forget.
The Jail of Fail got him off the streets, out of Barb’s house (as well as her…you know), and maybe out of Greene County for the foreseeable future. This isn’t about teaching him anything. It’s dealing with him.
He could live in a tard home which takes most of his tugboat as payment for his room and board. In Virginia, the court has to set him up somewhere within 30 days of his release (IIRC, sorry if I got something wrong, Legal Kiwis). It’s been speculated that this is another reason why everything is taking so long: finding somewhere to chuck him is difficult.