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The current situation with respect to this topic is that unless a rental property activity rises to the level of a "trade or business", small landlords are not required to send 1099s to service providers.
Although there is no objective definition of what constitutes a "trade or business", it generally has to do with the level of activity, etc., in the case of rental units, a 3-family rental property would not constitute a "trade or business" (the IRS would classify this as a passive activity) while 25 such properties with a full time manager, would most likely be classified as an active "trade or business" and would require issuing 1099s to service providers.
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