Most owners choose a property manager by instinct, a referral, and a headline number. The trouble is that the headline number, whether a management fee or a promised rent, tells you least about how the manager will behave once your keys change hands. That behaviour is written into the smaller mechanics, and questions are how you draw it out before you sign.

This note is a working checklist, grouped by the six things that tend to matter most. Ask plainly, and watch the ease of each answer as much as the answer itself.

Maintenance and who performs it

Maintenance is where a manager's incentives show most clearly, the one recurring cost a manager can either control on your behalf or quietly earn from.

Do you add anything, a percentage or a coordination fee, to invoices from trades?
Can I see the original invoice from the trade, rather than a summary line?
Who chooses the trades, and do they pay you anything to be chosen?
Are supplies billed at the price you actually paid for them?

A manager who bills at cost answers these in under a minute. One whose model includes a markup reaches for softer language, and that softening is itself information, since a markup changes what the manager is rewarded for, as we describe in why maintenance should cost you wholesale.

What the statements look like

Ask for a sample owner statement before you sign anything, then try to audit it. Three questions settle most of it:

Can you trace every dollar of income to a specific stay, with its dates and the rent collected?
Can you open the source receipt behind every expense line, rather than a category total?
Can you recompute the management fee yourself from the numbers shown?

If any answer is no, ask why. A line that reads "maintenance and repairs" with no invoice behind it is a claim, not a record, and vague statement lines are where the fees outside the headline percentage tend to live, a standard we describe in what full transparency looks like in an owner app.

How the price is set and updated

A price chosen on the day a listing goes live is competing against a different market within a few months, as holidays pass and the seasons move demand around the city. The useful question is how the price changes after the first guest arrives.

Is the rent set once, or does it adjust as the market moves?
What does the pricing actually read: holidays, local events, market rates, current occupancy?
Who decides when to raise or lower the number, and how often does it happen?

For stays of a month or more, each booking carries weeks of revenue, so the starting rate matters far more than any single night, and pricing should be a system rather than a fixed setting.

How guests are screened

Almost everything a manager promises rests on one upstream decision: who is allowed to book, and occupancy, review scores, and the condition of the furniture all trace back to that moment.

What checks run before a guest is approved: identity, credit and fraud, booking history?
Who are the typical guests, and where does the demand come from?
What happens when an applicant does not pass?

In our experience the strongest guest base for medium term stays is corporate: relocations, project teams, and professionals on contracts, screened with identity and credit fraud checks and pattern recognition, because those guests behave well and tend to extend. A manager who cannot describe screening in specifics is telling you it is not happening.

How occupancy is proven

Occupancy compounds, because an empty week earns nothing and can never be recovered, and it is the number most often asserted and least often shown.

What is your occupancy across the portfolio, and how is it measured?
How does that compare with similar nearby listings?
Can you show it in a statement, not just a slide?

A figure with no method behind it is marketing. Our own occupancy sits at 98% across the portfolio to date, 51% higher than similar nearby listings, from pricing, screening, design, and referrals working together, as we set out in what 98% occupancy actually takes.

References from current owners

Finally, ask to speak with two or three owners the manager works with now, not a curated testimonial. Owners will tell you what a contract cannot: whether the statements are easy to read, whether problems were handled without drama, and whether they would sign again. A manager confident in the relationship makes the introduction quickly.

If you would rather begin from real numbers for your own unit, the modeling is free, and the waitlist is where to ask for it. We model every property before accepting it and take homes only when confident we can outperform the market, and when the numbers fall short we say so.

Frequently asked questions

What should I ask a property manager before signing?

Ask how maintenance is billed and whether you can see the trade's invoice, whether you can audit a sample statement, how the rent is updated, how guests are screened, how occupancy is proven, and whether current owners will speak with you.

How do I know if a property manager is trustworthy?

Trust is easier to test than to sense. Ask for a sample owner statement and try to trace every dollar and open every receipt, ask for the occupancy method behind the headline figure, and ask to speak with current owners. A manager who bills at cost produces all of it without friction.

What questions reveal hidden fees in property management?

Ask whether anything is added to trade invoices, whether supplies are billed at the price paid, and whether there are onboarding or renewal fees beyond the stated percentage. Then check that every expense line carries a receipt, since vague category totals are where charges outside the headline fee tend to hide.

Questions to ask before hiring a property manager