Very unfortunate for the kid and you and the neighborhood by the sound of things. It sounds like the mom has "taught" the kid to follow in her footsteps (you make it sound like she's a deadbeat, living off the govt teat). Seems like the family (grandparents and aunt) could be supportive of the kid (I would think that with that much family around, he's eating just fine). Or maybe his family has realized that he's going down the wrong path and have pulled back on assistance.
I hadn't read to the end of your post before I started thinking something similar "the kid needs a talking to" and "how could this be broached?"
LMAO! WDF would be the perfect person for this delicate situation.
Honestly, I'm not that good with people, so my solution would probably be to pull back, lock up my stuff, and be a little sad. I also feel like this could turn into one of those "no good deeds..." situations. But I think that your approach is probably the best, and fits with the "it takes a village..." sort of thing.
I look forward to the advice provided by the group. There's almost always good advice from someone on this sort of thing eventually.
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Steve
'08 Boxster RS60 Spyder #0099/1960
- never named a car before, but this is Charlotte.
'88 targa

SOLD 2004 - gone but not forgotten