Listen...
He always plays the innocent good guy who's kind and generous. People that are kind and generous don't tell you that they are. Other people tell you.
Red flags all over
Yes. And I wouldn't trust him with much for that very reason but socially awkward people might do that, too and never hurt a fly, so I wouldn't call him a scammer just by gut feeling. Show me proof of harm and I'm the first to call him out.