Send a blank Form W-9 to every vendor who worked on your rental this year, today, before anyone is thinking about tax season. You need a name, an address, a taxpayer identification number, and a business type. Collecting that in November takes one email. Collecting it on January 28 from a plumber who has moved on takes a week and sometimes never works at all.
That is the practical answer. The legal answer has three parts, and they are worth separating because landlords tend to argue about the wrong one.
Part one: is your rental a trade or business?
Form 1099 reporting applies to payments made in the course of a trade or business. The instructions are blunt about the other side of that line: personal payments are not reportable, and you are engaged in a trade or business if you operate for gain or profit.
Where does a rental sit? There is no bright line in the statute for landlords, and that is genuinely the state of it. A landlord with a dozen units, a business bank account, and vendors on retainer is running a business by any ordinary reading. Someone renting an inherited condo to a cousin at cost is further from it.
Schedule E does not let you skip the question. Line A asks whether you made payments that would require you to file Forms 1099, and line B asks whether you filed them. You answer both, under penalty of perjury, on the same page as your rents.
If you are in the middle, that is a question for a CPA who can look at your whole situation. It is not a question to answer by deciding you would rather not file.
Part two: the threshold moved
For a long time the number was $600. It is not anymore.
For tax years beginning after 2025, the minimum threshold for reporting these payments rose to $2,000, and it may be adjusted for inflation beginning in calendar year 2027. The older threshold still governs payments made in earlier years, so if you are cleaning up a prior year, use that year’s number.
A few specifics survive the change and are easy to trip on:
- Attorneys’ fees of $2,000 or more paid in the course of your business go in box 1a of Form 1099-NEC.
- Gross proceeds paid to an attorney, the settlement-money case rather than payment for the attorney’s own services, are reportable at $600 or more in box 10 of Form 1099-MISC.
- Payments to corporations are generally exempt, with legal services a standing exception. A vendor operating as an S corporation usually does not get a 1099; the same person operating as a sole proprietor does. The W-9 is how you find out which.
- Rents you pay get reported in box 1 of Form 1099-MISC at $2,000 or more, but not when you paid them to a real estate agent or property manager. In that arrangement the manager reports the rent it passes on to the owner.
Part three: the dates, which did not move
Form 1099-NEC is due on or before January 31 under section 6071(c), whether you file on paper or electronically. That same copy goes to the vendor.
Form 1099-MISC runs later: February 28 on paper, March 31 if you file electronically.
If a due date falls on a weekend or a legal holiday, it moves to the next business day. That is the only slack in the schedule.
One more date-shaped rule. The electronic filing threshold is now 10 returns, counted by aggregating all your information returns, effective for returns required to be filed on or after January 1, 2024. A landlord filing eleven 1099s cannot mail them.
What to actually do, in order
- Ask for the W-9 before the first payment. Make it part of onboarding a vendor, next to the insurance certificate. A vendor who will not provide a TIN is telling you something.
- Pay vendors from the rental account. Cash payments are still deductible if you can substantiate them, but they are invisible to any year-end total, which means you will be reconstructing the year by memory.
- Run the vendor total in early December. Anyone over the threshold needs a form. Anyone close to it needs a look, because a December invoice can push them over.
- File by January 31. Then check line A and line B on Schedule E honestly, because you just earned the right to.
Where the record has to live
None of this is hard if the payments were categorized when they happened. It is miserable if they were not, and the misery is entirely in step three: adding up what you paid one plumber across a year of invoices, bank lines, and a couple of reimbursements.
LeaseRooster keeps vendor payments on the vendor and on the unit as you approve them, so the year-end total is a report rather than an archaeology project, and it can file 1099-NEC and 1099-MISC forms through an e-file provider when the totals are ready. Tracking vendor invoices and repair costs covers the capture side, and the vendor and work order tools are where the payments get attached in the first place.
When January comes, the tax season checklist puts this step in its place in the sequence.
This is general information, not legal or tax advice. Rules change and local ordinances vary. Confirm current requirements with your city, county, or an attorney before you act, and talk to a CPA about your own return.