Carl, it is not just to "individuals". In most cases, 1099-MISCs are for non-corporations. So "Bill's Lawn Service" would likely need a 1099. "Bill's Lawn Service Inc." would not. The only way to know for sure is to have the contractor fill out a W-9 before you pay them.
The 1099-MISC is only required for a "Trade or Business". Because it can be a "gray area", many people do not treat their rentals as a "Trade or Business" and don't send out 1099-MISCs. It is probably not a big deal. Until now.
The recently released Proposed Regulations for §199A say that only "self rentals" and "§162 rentals" qualify (§162 is for a "Trade or Business"). Although there are only the Proposed Regulations, as of now, that is what the IRS is stating. So if the rental property shows a taxable profit, it would be quite advantageous for a rental to be classified as a "Trade or Business" to potentially qualify for the 20% deduction.
