I have three rentals myself and pay a guy well over $600 for yard care and other help turning the property around when I have a property vacant between renters. I've never issued them a 1099-MISC and always select "no" for the 1099-MISC. It's never been a problem.
Now a number of years back congress passed a law that, in the way it was worded I was "required" to issue the 1099-MISC. But that same year congress revised the wording so that it didn't apply to rental property owners if rental income was not your primary business and primary source of income. So if you are not a real estate professional, just select no and press on.
