It is easy to get into trouble, with 1099, if you miss a couple of them, easy to do when you get mulitible ones, or when they sewer send them, (NEVER SEND THEM), then years later, you get a notice, you owe,$$$$$, plus interest and penaties, 100's turn it 1000's. And it takes years to slowly pay them off. As long as you have an agreement in place to pay the IRS back, most insurance companies, will appoint you. Just disclose everything to the DOI and the insurance companies.