I own two rental houses, pay for all sorts of expenses that exceed $600/yr. E.g. lawn service - $100/month; $1,200 per yr. Another example would be a painter I paid $1,500 during my last vacancy. I pay both in cash or check, get hand written receipts. Do I really need to generate a 1099-NEC for these guys? I don’t have an SS# or TIN for either (probably don't want to give it to me). Does every landlord generate this 1099 for every person they pay over $600/yr?
Related TurboTax question: when entering Rental (Sched E) info, one question is “Did you Pay Anyone $600 or More…”. I click “Yes, I paid for work …”. Then I click “No, I did not issue 1099’s”. Then Continue. So far, seems OK (those responses are factual). But have I set off an audit alarm?