[Paul K]

Grady,
some excellent advice here. My main concern would be that you are helping him to help himself- and that he will not become dependant upon, nor take advantage of, your generous spirit. It may be wise to set a timetable for the help you will provide, and some ground rules- no drugs/drinking/trouble with the law. If you believe in him, this may be what he needs to thrive & grow. Has he actually asked for anything or is he just sussing you out? I think an honest face-to-face is a good idea, it might give you a feel for how genuine this guy is. If he genuinely needs and will appreciate your help, I think you should give it, as outlined above.

Cheers,

Paul.