We currently have an outside person doing repos for our bank. We have never filed a 1099 on him in the past. I have just taken over the A/P area and I say we have to. Is there an exclusion for this type of work that I am missing? Of course, our Repo man says that he will retire if we start sending him one.

Of course he will - he doesn't want the fact that he has been evading taxes all this time to catch up with him.

Any non-employee individual or business that you pay $600 or more to during the year must receive a 1099-MISC. (I think corporations are exempt.) You also need to get a W-9 from them, certifying that they're not subject to backup withholding.

So if you've paid him more than $600, you have to file a 1099-MISC. Tell him if he wants to work for $599/year, you won't have to file!