It seems likely he has sent the email before based on the last paragraph. Doesn't mean he isn't sincere, just an observation.
If I was asking a pittance for the bike to begin with, I'd consider the idea of financing, with the understanding I might not get payment
#2 . If I needed the money and/or the price is significant, probably not...I'm all for being generous, but there are more needy people than some randon who is trying to go through college without debt.