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I think I am luck out here.  I paid the lawyer in two payment, half of it in 2023 December and the rest in 2024 Feb.  With your method, the rental portion for what I paid in 2023 will be less than 600 and so I will just report it as part of "Legal & other professional" category in rental income expense.

 

Side question, we also paid a company to do our rental's external painting and of course more than $600.  I am reporting it as expense.  Do I need to issue 1099 NEC to the painting company?