@TaxGuyBill Even so, 1099's are only necessary if you paid an *individual* more than $600 during the tax year. If you paid another business, such as the bug sprayer or even your licensed yard man (if yard care is included with your lease), the 1099 is not necessary.
Now it can be tricky with the yard man. If you make your checks payable to him personally, with his name on the check, then I would consider that "paying an individual" and do the 1099 *maybe*. However, if you make the check payable to "Bill's Lawn Service" then you're paying a business and the 1099 is not required.
I've been a landlord for 25 plus years with three rentals, and have never issued 1099's. Ever. I've had new roofs, new windows and quite a few other things in that time that each easily costs over $600. Not once was a 1099 issued. Of course, I don't hire "individuals" to do such big jobs either. I hire businesses who specialize in the work I need done.
As for the new 20% deduction, I've not really read up on that other than to peruse the new rules on it. From what I've read so far, I get the distinct impression that only applies to a business that has W-2 employees. But then, I've only perused the HR bill which requires some rather deep comprehension. I'd much rather deal with reading the IRS pubs on it, if they ever come out in a timely manner.
Now I'm not all that great with "Statutes", but as soon as I post this I'm googling §199A and will see if I can make sense of it, as it applies to me as a landlord.
