My rental property operates as a business since this is my sole source of income. I meet all the qualifications as a rental property professional and meet the hourly requirements on an annual basis.
In 2020, my mobile home park was hit by Hurricane Sally and suffered significant tree damages. Thirty-three trees were lost, some of them destroying homes.
I paid several tree companies to have these trees cut up and removed, exceeding the $600 threshold for 1099 requirements. Do I need to send 1099's to these companies? Do I need to write off the cost on taxes as casualty losses? Am I required by law to have them complete a W-9, or can I just call them and get their tax ID number, address, etc.?
If they report their tax income as self-employment income, on a partnership return or as an S corporation, as opposed to a traditional C corporation, then technically you are required to issue them a 1099-NEC form.
Of course you won't know that, so the safe thing to do would be to request that they complete a W-9 form and issue them the 1099 form. As a practical matter, if they are a large company, as opposed to an individual, it is not normally done.
Going forward ... it is best to determine this BEFORE you pay them anything ... if they will not willingly fill in a W-9 form then bid them good day and find someone who will. Also pay by check or better yet credit card ... never pay in cash if you can help it. If you pay anyone by credit card and get a company receipt you don't have to ever 1099 them.