How to Vet and Hire Contractors for Your Rental Properties (Without Getting Burned)

Every landlord eventually learns that the property doesn't make or break your returns — the vendor list does. A plumber who answers on Sunday, an HVAC tech who charges fair rates, and a turnover painter who shows up when promised will save you more money over ten years than any rent increase. This is how to build that bench: where to find contractors, how to vet them so you're not liable for their mistakes, how to price work correctly, and what paperwork the IRS expects from you at the end of the year.

Why contractor selection is a landlord risk issue, not just a cost issue

When you hire an unlicensed, uninsured handyman to replace a water heater and it floods the unit below, three things happen at once: your insurer starts asking uncomfortable questions, your tenant has a habitability claim, and you have no one to pass the bill to. Cheap labor is only cheap when nothing goes wrong.

There's a second, quieter risk: repair delays. In most states, a landlord's duty to maintain a habitable unit isn't excused because "the contractor was busy." If a tenant is without heat for a week because your only HVAC guy is on vacation, you own that problem — including potential rent withholding or repair-and-deduct remedies depending on your state. Redundancy in your vendor list is a compliance strategy.

The goal isn't the lowest bid. The goal is a short list of trades who answer the phone, do work that passes inspection, and carry enough insurance that their mistakes stay their mistakes.

Which trades you actually need on speed dial

For a small portfolio of one to ten units, you need two names in each of these categories — a primary and a backup:

• Plumbing — leaks, water heaters, sewer lines, drain clearing. Highest emergency frequency.
• HVAC — furnace, AC, heat pump. Seasonal demand spikes; book maintenance in shoulder months.
• Electrical — panels, GFCI, outlets, fixtures. Always licensed, never DIY-adjacent.
• General handyman — doors, drywall, caulk, hardware, minor carpentry. Your highest-volume vendor.
• Appliance repair — often cheaper than replacement on units under seven years old.
• Turnover crew — paint, clean, carpet. Speed matters more than perfection here.
• Roof and gutters — one inspection-capable roofer beats three storm-chasing salespeople.
• Pest control — recurring contract is usually cheaper than one-off callouts.

Where to find them

1. Ask other landlords first. Local landlord associations and REIA meetings are the highest-signal source, because the referral comes from someone with the same incentives you have: fast, cheap, done right.
2. Ask suppliers. The counter staff at a plumbing or electrical supply house know who buys quality parts and who buys the cheapest fitting on the shelf.
3. Ask your property inspector. Home inspectors see hundreds of jobs a year and have no financial stake in the referral.
4. Marketplaces last. Lead-gen platforms work for one-off jobs, but you're competing with homeowners paying retail. Use them to fill a gap, not to build your core list.

The five-minute vetting checklist

Before a new contractor touches a unit, confirm all five of these. It takes one phone call and one email.

• License status. Verify directly with your state or county licensing board, not from a photo of a card. Requirements vary widely — many states license plumbers and electricians at the state level while general contractors are licensed locally, and some trades have dollar thresholds below which no license is required.
• Certificate of insurance (COI). Ask for general liability and workers' compensation, sent by the insurance agent, not forwarded by the contractor. Request that you be added as an additional insured or at least as a certificate holder so you're notified if the policy lapses.
• Workers' comp specifically. If an uninsured worker gets hurt on your property, the claim can land on your policy. Sole proprietors are often exempt — get that in writing along with a liability policy.
• W-9 on file before the first payment. It is dramatically easier to collect a W-9 while you still owe money than after you've paid.
• Two landlord references. Not homeowner references. Ask: did they show up on the scheduled day, did the final price match the estimate, and would you send them to an occupied unit?

Questions that separate pros from problems

• "What's your typical response time for a no-heat call in January?"
• "Do you charge a trip fee, and is it credited toward the work?"
• "Will you text photos before and after? I bill some repairs back to tenants and need documentation."
• "Can you coordinate access directly with a tenant, or do you need me on site?"
• "What's your warranty on labor?" (30–90 days is standard for most trades.)

Pricing: how to buy repairs without overpaying

Landlords get overcharged in two predictable ways: paying retail homeowner rates and approving open-ended time-and-materials work with no cap.

• Under $300: approve by text with a not-to-exceed number. Don't burn a week collecting three bids on a $180 job — the vacancy or tenant frustration costs more than the savings.
• $300–$2,000: get a written scope with a fixed price. "Replace 40-gallon gas water heater, includes permit, haul-away, and expansion tank — $1,650" is a scope. "Water heater work" is not.
• Over $2,000: three bids, matched scopes, and a payment schedule. Never pay more than a materials deposit up front, and hold a final payment until you've seen the work or photos.

Ask about a landlord rate. Contractors will often discount 10–20% for repeat volume, prompt payment, and the absence of a homeowner hovering over their shoulder. In exchange, pay within 48 hours — being the client who never chases an invoice is worth more than haggling.

Handle permits deliberately

Panel upgrades, water heater replacements, HVAC changeouts, structural work, and most window or egress changes typically require permits. Unpermitted work can void insurance claims, complicate a sale, and in some jurisdictions expose you to fines or a forced tear-out. Make "permits pulled by contractor" an explicit line in the scope so responsibility isn't ambiguous.

Managing the job when a tenant lives there

Contractor performance in an occupied unit is half scheduling, half communication. Set expectations on both sides:

• Give the tenant a named vendor, a date, and a time window in writing — and comply with your state's notice-of-entry rules.
• Tell the contractor whether pets are present, where parking is, and whether shoe covers or drop cloths are expected.
• Require a photo of the completed work with the invoice. This is your evidence file if the same issue recurs or if the damage was tenant-caused.
• Follow up with the tenant 24 hours later: "Is the repair holding?" A two-line message prevents the same complaint reappearing in month three.

Those photos and invoices matter at move-out too. If you plan to charge a departing tenant for damage repairs, most states require an itemized statement backed by actual costs within a strict deadline — the specifics vary by state, so check the return window and documentation rules that apply to you before you deduct anything. Landlords in California, for example, face tighter itemization and receipt requirements than many other states. A vague "repairs — $600" line is how deposit disputes get lost.

Paperwork: 1099s, contractor vs. employee, and recordkeeping

If you pay an unincorporated contractor $600 or more in a calendar year for services on your rental, you generally need to issue a Form 1099-NEC. That's why the W-9 comes first. Keep in mind:

• Payments to corporations are usually exempt, but you still want the W-9 documenting that status.
• Payments made through a third-party network may be reported separately, but don't assume someone else is handling it.
• Missing or late 1099s carry per-form penalties, and a contractor who won't give you a W-9 is telling you something about how they run their business.

Classification also matters. If you dictate hours, supply tools, and direct the daily work of a "handyman" who works only for you, you may be looking at an employee — with payroll tax and workers' comp consequences. Genuine contractors set their own schedule, use their own tools, and serve other clients.

Finally, tag every invoice by property and by category (repair vs. capital improvement) as it comes in. A $400 faucet repair is generally deductible in the year paid; a $9,000 roof is capitalized and depreciated. Sorting that in April from a shoebox is where small landlords lose real money.

Key takeaways

• Keep a primary and a backup vendor in each core trade — redundancy protects you from habitability claims when your first call is unavailable.
• Verify license, general liability, and workers' comp directly from the licensing board and insurance agent before the first job.
• Collect a W-9 before you pay a dime, and issue 1099-NECs for $600+ in annual payments to unincorporated vendors.
• Match your approval process to the dollar amount: text approval under $300, fixed-price scope up to $2,000, three bids above that.
• Require before-and-after photos with every invoice — they're your documentation for tenant chargebacks and deposit deductions.
• Pay fast and be easy to work with; reliability from you buys priority scheduling from them.

Frequently asked questions

Can I do repairs on my own rental property myself?

Generally yes for cosmetic and minor work, but licensed trades like electrical, plumbing, and gas work are regulated in most jurisdictions, and permitted work may require a licensed contractor even on property you own. Beyond the legal question, DIY labor isn't deductible as an expense — only your materials are — and a botched repair in an occupied unit can trigger habitability and insurance problems.

Should I ask contractors to add me as an additional insured?

For recurring vendors and any job over a few thousand dollars, yes. Additional insured status extends the contractor's liability coverage to claims arising from their work on your property, and you'll typically be notified if the policy is canceled. For small one-off repairs, a current certificate of insurance naming you as certificate holder is usually sufficient.

Can I charge a tenant for a repair the contractor performed?

You can charge back repairs caused by tenant negligence or misuse if your lease says so — a clogged line from flushed wipes, a broken window, a pet-damaged door. You cannot charge back normal wear and tear or code-required maintenance. Keep the invoice and photos, bill it promptly rather than saving it for move-out, and follow your state's rules on what may be deducted from a security deposit.

How many bids should I get for a turnover paint job?

Two is usually enough once you know your market rate per square foot. On turnovers, days of vacancy often cost more than the price spread between bidders, so favor the crew that can start Monday over the one that's $200 cheaper in three weeks.

The bottom line

A vetted vendor list is infrastructure. Build it before the emergency, document it, and keep every invoice attached to the property and the work order it came from so repair history, tenant chargebacks, and tax categories are all in one place. That's exactly the workflow Rentmark is built around — maintenance requests, vendor assignment, photo documentation, and expense tracking that flows straight into your year-end numbers. You can explore the live demo without creating an account and see how a single repair moves from tenant report to categorized expense.