system
A chat on subreddit /r/NoStupidQuestions
human
I think if you just gave him the money itd be weird

But, if you also leave a letter explaining the impact he left on you, thatd be good

Although I wouldnt mention how you feel sorry for him, he might take that as pity, which many people dont like. Maybe mention how he reminded you of someone else though, and it's in a way, for them as well
gpt
GIVE HIM THE MONEY. That's solid help that will make a difference in his life (and maybe his relatives' lives if they're supporting him).