If you own a rental, you do not have to send Form 1099-Misc to your roofing contractor. That rule was repealed.
You do not need to issue a Form 1099 for investment rentals. The rules you refer to were not to be implemented until 2012 for payments made during 2012. They were repealed by HR 4. The President signed the repeal bill on April 14, 2011. In doing so, the requirement for rental property owners to issue Form 1099-MISC no longer exists for any year.
The exception may not apply to payments made for attorney's fees, which would still require Forms 1099.
Additional information:
Those rules were repealed under H.R. 4 (P.L. 112-9) and made retroactive, as if they had never been enacted. Therefore, landlords, in the ordinary situation of renting out a house or two, do not have to issue 1099s to service providers. In that situation, you would answer “no” to the first question, “Did you make any payments in 2011 that would require you to file Form(s) 1099?” The second question (“If yes …”) can be left blank.
There are still situations where a Schedule E filer would have to issue 1099s. In general, you would have to file 1099s if you materially participate (nonpassive) in the activity. For example, if you are a real estate professional and treat the rental activities as nonpassive, you are in a trade or business and you must issue 1099s.
See H.R.4
Comprehensive 1099 Taxpayer Protection and Repayment of Excvhange Subsidy
Overpayments Act of ... for additional information.
