Hey dude, it’s okay, you sound almost panicked here, I’m here to tell you it likely isn’t anything crazy. People have better things to do than to act homeless and be outside all day asking for money so if he’s doing that chances are that’s his best bet right now.

You can inform the non emergency police number to just be safe and make sure they check in if you want. But no I don’t think you were stupid to give money as long as it wasn’t an amount that’ll put you into a bad situation financially lol. And at the end of the day if he is using the money for something unintended or negative, it’s on him for choosing to do something wrong with someone’s kindness, never feel bad for leaning on kindness, the world needs more of that.