Endless loops of "Please pay me 2 cents via PayPal so I will read your message with the Subject: Please pay me 3 cents via PayPal"
Oh, you'll put in an exception for those messages?
Next message is from your mother. You're going to charge her 2 cents?
Ah, whitelists. Management problem.
Also: PayPal can't efficiently handle micropayments. (Well, for 33 cents apiece, they will.) So you need your own micropayment system. Which will be incompatible with your prospective customer's micropayment...