I have to agree, though I understand how one's feelings could be mixed about it. The earlier description about him living out of his car and oversharing about his situation left me feeling sorry for him on the one hand, but on the other realizing that he sounded like someone who was in a situation that could leave him rather desperate - something that can lead to bad outcomes in any case. Him knowing that he'd scammed you previously might either embolden him or make him wary of you in any case.
Most likely best to let him go and move on.