First of all, I wouldn't allow you to send me that much cash in one transaction. I would insist that we trade in smaller denominations. Why aren't you willing to make smaller trades at first and go up from there once we have established a relationship?
This is yet another sign of bad practice. Requesting people to do only smaller transactions creates even less value as the transaction costs (time, mailing, etc.) are way to high.
Stop bothering us with your improper business model.
That's not a sign of a bad business model. That is a sign of intent to build a trust relationship. If he had asked someone to send more at a time, then I'd be suspicious. Start with, say, $20. At that level, the cost of the stamp is still favorable to paypal. If you wish to save as much on the stamp as possible, consider doubling your cash with each transaction. This way if this thing turns sour, there is no point at which either party could have done
significant harm. If you double until you get to an uncomfortable level, stop doubling; and this protects you from dishonest mailmen from doing significant harm.