Question: does a landlord need to issue 1099s to contractors who perform work on the landlord's property? Answer: I give a CPE presentation on Form 1099, and I've also done far more research into 1099s (especially 1099-MISC) than any sane person should. And I can say, I have an opinion on the answer to this question [...]
It's a holiday week so I'm re-posting popular blog posts from the past. This post from January 2013 deals with allocating basis in a rental property between the house and the land.
This is a rare case where I can give a straight, firm answer: the 1099 should show the gross amount of rent collected.
This happened a number of years ago, in the early days of my business, and it was the first time I had to deal with a situation that kept me up at night. But after much research and discussion with other tax pros, I felt comfortable with the way we reported the loss.