Who We Help · US Rental Owners · Payroll
Payroll for US rental owners: manager, caretaker, or contractor?
Most Canadian owners of a US rental never need payroll — and keeping it that way is usually the right call. Your property manager should be a vendor, your handyman a contractor, and the paper trail of W-9s and 1099s is what protects that setup. Hire a person directly — an onsite caretaker, say — and you become a US employer, with federal and state obligations that have nothing to do with the CRA.
By the AnalytIQ Accounting team · Last reviewed: August 12, 2026
Most owners never need US payroll — protect that position
A property management company is a vendor, not an employee. It invoices its fee, hires and pays its own staff, and carries its own insurance. That arrangement keeps you out of the US employment system entirely, and for a Canadian owner of one or two rentals it is usually the right end state. The paperwork that protects it is boring: a signed management agreement, monthly statements, and an invoice behind every repair.
The line moves the moment a person — not a company — works under your direction. An onsite caretaker you schedule, a handyman who shows up most weeks with your task list and your tools, a leasing helper you pay hourly: under the IRS common-law test (behavioural control, financial control, and the relationship between the parties), those look like employees no matter what the two of you agreed over the phone. Many states then apply their own, stricter tests on top for unemployment insurance and workers comp.
Vendor, contractor, or employee — where each helper lands
Classification decides the paperwork, and the pattern is consistent enough to put in one table:
| Who does the work | US treatment | Your paperwork |
|---|---|---|
| Property management company | Vendor | Invoices on file; usually no 1099 because most are corporations — the W-9 confirms it |
| Self-employed handyman or landscaper | Independent contractor | W-9 before the first payment; 1099-NEC if your rental activity is a US trade or business |
| Onsite caretaker you schedule and direct | Employee | EIN, Form 941 withholding and FICA, Form 940 FUTA, state unemployment, W-2, usually workers comp |
| Cleaner at the personal-use vacation home | Household employee | Schedule H and a W-2 — household rules, not business payroll |
The household-versus-business line most owners miss
The same worker can sit under two different rule sets depending on which property they serve. A caretaker at a rental property is a business employee: real payroll, Form 941 deposits, FUTA, state registration — and the wages deduct against rental income. A cleaner at the vacation home your family actually uses is a household employee: no quarterly 941s — the employment taxes are reported once a year on Schedule H — but still a W-2, and the cost is personal, not deductible.
Mixed-use properties are where this goes wrong. If the house is rented forty weeks and personal for the rest, the worker's status and the deductibility of their cost need to be allocated deliberately, not reconstructed in April. We set the split when the worker is hired, not after.
If a caretaker does turn out to be a business employee, the mechanics are manageable but unforgiving on timing: the EIN and state registrations have to exist before the first pay run, federal deposits run on a schedule the IRS sets for you, and workers comp should be bound before the worker sets foot on the property — an injury in week one with no coverage is the worst version of this story.
1099-NEC: a small form doing a lot of protective work
Collect a W-9 from every US contractor before the first payment — after a dispute is too late. A contractor who will not provide a TIN is a contractor you must backup-withhold 24% from, and that conversation goes better up front.
- Threshold: 1099-NEC applies once payments reach $2,000 in 2026 — the long-standing $600 threshold was raised starting with 2026 payments.
- Who is exempt: corporations, which is why management companies rarely receive one.
- Trade or business: the filing duty attaches to business payers. A self-managed rental with regular activity usually qualifies, and filing is cheaper than litigating the point.
- Foreign helpers: a Canadian contractor working physically in Canada gets a W-8BEN in your file, not a 1099.
The Canadian side of your US people costs
Nothing above touches CRA payroll. US workers never appear on a T4, and you cannot run them through a Canadian payroll platform — employment taxes follow where the work happens. What crosses the border is the deduction: caretaker wages, management fees and contractor invoices reduce the same rental income you report to the CRA, converted to Canadian dollars, with foreign tax credits doing the reconciliation. The full framework sits on our page for Canadians owning US rental property.
If you also pay Canadian help — a bookkeeper, or a virtual assistant handling tenant emails from Ontario — that is a Canadian-side cost, and fees to unincorporated Canadian contractors can carry a T4A obligation. We run the US side on tools like Gusto and the Canadian side on Wagepoint, so every worker is paid, and reported, in the right country. Fixed fee, quoted after a discovery call.
Common questions.
Do I need to send a 1099 to my property management company?
Usually not — most management companies are corporations, which are exempt from 1099-NEC. Collect a W-9 anyway: it documents the exemption and protects you if the manager turns out to be a sole proprietor.
My caretaker prefers to be a contractor. Can we just agree to that?
No. Classification follows the facts — who controls the schedule, methods and tools — not the contract, and many states apply tests stricter than the IRS one. A written agreement only helps when the facts already support it.
Can I pay my US caretaker through my Canadian company's payroll?
No. US employment taxes apply where the work is performed, so a US worker needs a US payroll: EIN, federal deposits, state registration and a W-2. We set that up alongside your Canadian reporting.
Related reading
People costs handled on both sides.
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