How to Track Contractor Wages and Payments in DeductFlow
Most STR hosts pay cleaners, handymen, and property managers as independent contractors. Managing those payments carefully—collecting W-9s, tracking the $600 threshold, and generating 1099-NEC summaries—is a legal requirement and a significant deduction. Here's how to do it in DeductFlow.
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Who Counts as a Contractor for 1099 Purposes
| Worker Type | 1099-NEC Required? | Notes |
|---|---|---|
| Cleaner / housekeeping (individual) | Yes (if $600+) | Most common STR contractor |
| Handyman / maintenance (individual) | Yes (if $600+) | Includes plumbers, electricians (sole prop) |
| Property manager (individual or LLC) | Yes (if $600+) | Single-member LLC treated as individual |
| Cleaning company (Inc. or S-Corp) | Generally No | Corporations exempt from 1099-NEC* |
| Contractor paid via Airbnb co-host | No | Airbnb handles their tax reporting |
*Check the W-9—if the business is an S-Corp or C-Corp, box 3 or 4 will be checked. Attorney fees to corporations are still 1099-reportable regardless of entity type.
Step-by-Step: Tracking Contractor Payments
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1
Add a Contractor as a Vendor
Navigate to Contractors > Add Contractor. Enter:
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- Legal name: Must match their W-9 exactly (individual name, not nickname)
- Business name: If they operate under a DBA
- TIN: SSN (individuals) or EIN (businesses)—confirm via W-9
- Mailing address: Where the 1099-NEC copy will be mailed
- W-9 on file: Check this box once you've collected their signed W-9
Save the contractor profile. They now appear as a vendor option when logging expenses.
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2
Log Each Payment
Every time you pay a contractor, log it in DeductFlow:
- Navigate to Expenses > Add Expense
- Select the contractor from your vendor list
- Enter the amount, date, and description (e.g., "Cleaning – 3 nights, April 2026")
- Category: Contract Labor maps to IRS Line 11
- Property: assign to the correct STR if you have multiple properties
- Attach a receipt or payment confirmation if available
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3
Monitor the $600 1099 Threshold
In the Contractors section, each contractor shows a running payment total for the year. Color coding alerts you when action is needed:
- Gray — Under $600; no 1099 required yet
- Yellow — Approaching $600; prepare W-9 if not collected
- Red — Over $600; 1099-NEC required by January 31
You can also filter your contractor list by "1099 Required" to see only those who cross the threshold at year-end.
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4
Generate the 1099-NEC Summary Report
Navigate to Reports > 1099 Summary. Select the tax year. The report lists:
- Contractor name and TIN
- Total payments made during the year
- Payment method (check, ACH, Venmo, etc.)
- W-9 on file status
- Any contractors with missing TIN flagged
Download as PDF and share with your CPA, who will prepare the actual 1099-NEC forms and file copies with both the contractor and the IRS by January 31.
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5
Export for Filing via 1099 Service
If you or your CPA uses a 1099 filing service (Tax1099, Yearli, Gusto, etc.), export the contractor data as CSV from DeductFlow and import directly into the filing platform. The CSV includes all required fields:
- Recipient name and TIN
- Box 1 NEC amount
- Address for paper copy mailing
- State and state ID if required
E-filing is required for filers submitting 10 or more 1099 forms (as of 2024 IRS rules). For smaller portfolios with fewer than 10 contractors, paper filing is still permitted.
W-9 Information to Collect for Every Contractor
- Legal name (Line 1 of W-9)
- Business name / DBA (Line 2, if applicable)
- Federal tax classification (sole prop, LLC, corporation)
- Taxpayer Identification Number (SSN or EIN)
- Current mailing address
- Contractor's signature and date
No credit card required
1099 Season Starts Day One—Track Every Payment
DeductFlow tracks contractor payments year-round, flags the $600 threshold automatically, and generates the 1099 summary your CPA needs to file on time. No scramble in January.
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