Buster,
I think if you are having a hard time trusting him right now, you should really monitor what he uses the money for. Ask questions and ask for receipts, and when he doesn't bring them back to you, that trust will be lost. Anyone can get a receipt for anything, so he really shouldn't have any excuses!
But i don't really think yoyu should be handing out YOUR hard earned money when you don't really know if he's getting what he says. I say, test him a couple times, see if he brings back what he says he's going to, or a receipt, that way he will have the chance to actually BUILD or BREAK trust with you.
Let us know how it goes...
Lotsa Love
T