There's another question you have to ask FIRST. Is your rental property a "Business"? Only if your rental activities "rise to the level of a business" do you need to file 1099.
Not all rental activities are businesses. Most owners of rental properties not engaged in other real estate do not rise to that level and do not need to file 1099 for contractor payments. (confirmed with a turbo tax consultant/live help). Unfortunately, Turbo Tax's automated question about 1099's is only a YES/NO question (did you pay a contractor more than $600) but should include the option "you are not engaged in a trade or business" which exempts the 1099 requirement. Instead, the consultant advised me to select "NO" because my one rental home (which I inherited when my Dad passed and quickly rented to pay his mortgage) was not a "business", nor was I engaged in any other real estate business.
I would never had been able to figure that out just by answer YES/NO to that question. I did pay more than $600 to a contractor/handyman to do work in my rental but my activities did not rise to the level of a business and I did not need to file a 1099. It took me 3 different "Turbo Tax Consultants" to figure out how to bypass it without simply "lying" and answering "NO", I didn't pay a contractor more than $600. This needs to be fixed by Turbo Tax.
"The AICPA tried to clear up the confusion among its members with an article about 1099 requirements for rental properties and also wrote an open letter to the IRS in 2013 to express its position and request further guidance. It is the position of the AICPA that landlords only need to file form 1099 when their rental activities rise to the level of a trade or business (Porter). This means that most owners of rental properties who are not engage in other real estate business do not need to file 1099 forms."
IRS.GOV
You are NOT required to file information return(s) if you are not engaged in a trade or business.
