Q. I realize that I should have sent a 1099 for my rental to the company that did some maintenance as I paid them over $700 last year. Is it too late to file a 1099?
A. Yes and no. Yes, technically it is late to be sending your maintenance company the 1099 as it was due by January 31. No, it is not too late to file the 1099 with the IRS. You have until February 29th (Leap Year) to do this. One quick suggestion: Since you plan to send the 1099 to the IRS, I would send it to the recipient late. Any legitimate company will report all income regardless of whether a 1099 is issued or not.