Well, on first hearing I would say be careful. There are many many ways scammers have to scam you.
On the other hand . . .
You've known this guy now for a number of years, and you're still wondering if you're being scammed? That in itself is a bad sign in my opinion.
I think others here who are older and/or wiser than I will be better at answering, but that's just my stab in the dark
