I think what you are saying is that you want to make sure that the contractor reports the income. That's not your responsibility, and if he doesn't report it it's not your problem. You will not have any problems with the IRS, no matter whet the contractor does. I would put it a little more strongly that DoninGA did. Not only are you not required to issue a 1099, you are not supposed to issue a 1099. The IRS does not want you to issue one. If you want to do everything above board, follow the IRS rules and do not issue a 1099.
