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LANDLORD RESOURCES & FIELD GUIDES

Plain-English guides to protect your cash flow and avoid tax-time surprises.

Most independent landlords aren't CPAs, construction managers, or real estate attorneys. Use these practical checklists to run your rentals with confidence.

TAX & COMPLIANCE GUIDE 5 MIN READ • CONTRACTOR PAYMENTS

When Do Landlords Actually Need a Signed W-9 and Form 1099-NEC from a Contractor?

Every January, thousands of landlords scramble to track down contractors they paid months ago—wondering who needs a 1099-NEC and who doesn't. The good news: not every contractor requires a W-9 or 1099-NEC. Everything comes down to three simple questions.

QUESTION 01

How Did You Pay Them?

If you paid by Credit Card, Debit Card, Stripe, or PayPal/Venmo Business, you do NOT need to file a 1099-NEC. The card processor reports the payment on Form 1099-K. If you paid by Check, ACH, Cash, or Zelle, the reporting responsibility stays with you.

QUESTION 02

Was It $600+ in the Year?

If your total payments to that contractor across the calendar year are under $600, no 1099-NEC is required—simply save the itemized invoice for your Schedule E tax deductions. Once cumulative payments hit $600 or more, reporting rules apply.

QUESTION 03

What Is Their Tax Structure?

Sole proprietors, handymen, single-member LLCs, and partnerships require a 1099-NEC. S-Corporations and C-Corporations are generally exempt—but collecting a W-9 is the only way to prove whether an "LLC" is taxed as a sole proprietor or an S-Corp.

Landlord Payment Scenario Collect W-9? File 1099-NEC? Why It Matters
Paid by Credit Card, Debit Card, or PayPal Goods & Services No No Card networks issue Form 1099-K automatically (IRS Sec. 6050W). Sending a 1099-NEC double-reports their income.
Paid under $600 total for the calendar year (e.g., $220 lock repair) No* No Below the $600 annual threshold (*unless a second job later in the year pushes their total over $600).
Paid $600+ by Check, ACH, Cash, or Zelle to a Handyman / Sole Prop / LLC Yes Yes Zelle does not issue 1099-Ks. Collect the signed W-9 before releasing the final check.
Paid $600+ by Check, ACH, or Zelle to an S-Corp or C-Corp Yes (Once) No Corporations are exempt from 1099-NEC, and their signed W-9 on file is your audit-proof record of that exemption.
Bought Materials Only (e.g., Home Depot, Lowe's, supply house) No No Purchases of physical goods/materials alone do not require a 1099-NEC.
The Golden Rule of Timing: Never ask for a W-9 while a contractor is just giving you an initial estimate, and never wait until January when the job is long paid. If you are paying $600+ by check, ACH, or Zelle, request the W-9 alongside their final invoice before you hand over the check.
REPAIRS & CONTRACTS 4 MIN READ • RISK PROTECTION

6 Things Every Contractor Estimate & Final Invoice Must Have in Writing

A one-line quote that says "Roof repair — $1,300" leaves a landlord exposed to surprise change orders, cheap materials, and zero recourse if the leak returns next month. Before you approve any repair, make sure these six items are written directly on the estimate and final invoice:

1. Written Workmanship Warranty

Manufacturer warranties only cover defective materials—not poor installation. Always require a written labor/workmanship warranty (typically 1 to 3 years) on the estimate and invoice.

2. Specific Material Grades

Don't accept generic terms like "shingles" or "paint." Specify architectural shingle grade, pipe material, or fixture model so builder-grade substitutes aren't used.

3. Debris Haul-Away Included ($0 Extra)

Many contractors tack on a $150–$300 "dumpster or disposal fee" on the final bill. Confirm upfront that site cleanup and haul-away are included in the all-in price.

4. $0 Change-Order Cap Without Approval

Include a simple line: "No additional charges exceeding $0 without prior written approval and photos from the owner." This stops surprise add-ons cold.

5. Start & Completion Dates

Locking in clear start and finish dates lets you coordinate your calendar, give proper 24–48 hour legal entry notice to your tenant, and avoid half-finished jobs.

6. Tax-Ready Final Invoice Details

For your CPA and IRS Schedule E records, the final invoice should clearly show the contractor's business name, address, property address serviced, date completed, and itemized labor vs. materials.