Do I need to send my handyman a 1099?

ben_spreadsheets Starter postOct 30, 2026

I paid my handyman about $3,200 this year across all three rentals, mostly by check, some by Venmo. He is just a guy, not a company. Do I need to send him a 1099 for this, and what do I need from him?

6 replies

  1. mel_accidentalOct 30, 2026

    There is also a question about whether your rentals count as a trade or business for this. My preparer said with three rentals and records like yours, just file them. Easier than arguing about it.

  2. ben_spreadsheets AskerOct 30, 2026

    Getting a W-9 from him this week and asking my preparer about the threshold and the Venmo part. Thanks.

  3. pete_handyOct 30, 2026

    As the handyman, I would rather fill out a W-9 at the start than get chased for it in January. Just ask for it before the first job.

  4. gary_2rentalsOct 30, 2026

    Payments through a card or an app like Venmo set up for business are usually reported by the payment company, not you. So you may only count the checks. Your preparer can sort that out.

  5. kelly_officeOct 30, 2026

    We send 1099s to any individual vendor over the threshold, paid by check or cash. I read the threshold went up from $600 to $2,000 for payments made in 2026, so ask your preparer which applies to your year. Get a W-9 from him either way.

  6. LandlordPro AI AI-generated answerOct 30, 2026

    Dealing with year-end paperwork for independent contractors can definitely feel a bit confusing at first. Even though your handyman operates as an individual rather than a formal company, the total amount you paid him during the year pushes past the standard reporting threshold used by many landlords. The exact dollar limits and specific rules can vary depending on your location and tax year, so it is always smart to double-check with your tax professional or local tax agency. To get this sorted out properly, you will want to request a completed Form W-9 from him to collect his correct legal name, address, and taxpayer identification number. This form ensures you have all the right details on hand before you file your information returns.

    Generated by AI. Not legal, tax or investment advice, and it may be wrong. Check with a qualified professional before acting.

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