Investor · AMBLER, PA · Member since 2013 · 158 posts · 98 votes
Hello,
I had to perform some repairs to my roof and ceiling due to ice damming. Am I required to issue a 1099 to the contractor if the cost is covered by insurance? To be clear, insurance cut me the check and then I paid the contractor from the funds issued. I am asking in preparation for next year. I didn't realize that landlords were required to file 1099s and I don't want to be as unprepared next year as I was (am) this year. Also, if anyone can recommend some good tax related books for landlords, that would be great. I only have 1 property and am not really planning to get any more in the near future.
Investor, Entrepreneur, Educator · Springfield, MO · Member since 2009 · 21k+ posts · 12k+ votes
12y
Karen, yes, the fact that you received funds from a loss has nothing to do with you contracting work to be done. Money goes to you. You hire workers and pay them. You may pay them more or less than what you received. There's no relationship as to the source of funds and paying a contractor. Do the 1099s. :)
Rental Property Investor · Douglas County, MO · Member since 2014 · 1k+ posts · 1k+ votes
12y
It's always better to issue one that you didn't need to than to fail to issue one that you should have. The first has no bad consequences, the second can get you fined.