I appreciate the concerns on both sides, but if he is using a branch bank, find the nearest branch for him. Tell him to come check out the machine, then go cash the check and come back with cash.
I got burned several years ago with a cashiers check. They opened a checking account for $25, got a $5 cashiers check on the new account, washed the check and reprinted it for $255. Two weeks later, my bank pulled $250 out of my account (bouncing 3 or 4 checks along the way). I was out the computer equipment, $250 and had over $100 worth of bounced check and overdraft fees.
It is now a policy that, if I don't know you very well, cash is king, baby.
ken