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Owners·26 May 2026·7 min read

How to choose a property manager: the right questions to ask

Handing over your property is a significant decision. Here is how to genuinely assess who you are talking to before signing.

LC

Luca Chiacchio

Chiacchio Property Management

How to choose a property manager: the right questions to ask

Entrusting your property to a property manager means handing over operational control of an important asset. Done right, it can free you completely from day-to-day management. Done poorly, it becomes a problem.

The short-term rental property management market has grown rapidly. Not all managers have the same experience, standards or transparency. Knowing what to ask is the most effective way to tell them apart.

The questions that matter

About the portfolio and experience

"How many properties do you currently manage?" There is no universally right number, but a manager handling 200 apartments with a two-person team cannot guarantee the same attention as one managing 30 with a structured team. What matters is the ratio of properties to operational staff.

"How long have you been operating in this area?" Local experience counts: knowledge of demand patterns, specific seasonality, the most effective channels for that market, local authority procedures.

"Can I see results from properties similar to mine?" A serious manager has data. If they do not have it or will not show it, that is a signal.

About operational structure

"Who responds to guests at night or on weekends?" Guest management is not office hours work. Ask who covers out-of-hours situations and how emergencies are handled.

"How are cleaning and maintenance providers selected?" A professional manager has stable, vetted, long-standing providers — not an improvised network of contacts.

"How does check-in work?" Check-in is the guest's first physical contact with the apartment. It must follow precise procedures, not be left to improvisation.

About revenue management

"How do you set rates?" If the answer is "we look at competitors", that is a superficial approach. A real revenue manager uses demand data, conversion rates, booking window, local events.

"How often do you update prices?" Rates should be reviewed frequently, not occasionally. Ask how often and through which tools.

About transparency

"How is monthly reporting structured?" Ask for a sample report. It should be clear, complete, with bookings, gross and net income, commissions, costs.

"Can I access booking data in real time?" An owner has the right to know what is happening with their property. An accessible owner portal is not optional.

"How is the management fee structured? Are there hidden costs?" The most common model is a percentage of net revenue. Verify what is included and what is not: hidden costs (platform commissions, setup fees, extraordinary expenses) often change the final figure significantly.

Warning signs

Be cautious when:

  • no data-based estimate is provided upfront
  • communication is already slow or unclear during the initial conversation
  • there is no clear contract with defined exit conditions
  • no verifiable results from other properties are shown
  • occupancy rates of 95% or guaranteed income regardless of season are promised — figures that cannot be sustained

What to look for in the contract

Before signing, check:

  • duration and termination: how much notice is required to exit? Are there penalties?
  • exclusivity: are you prevented from using other sales channels?
  • who manages payments: does the manager receive payments and remit the net to you, or do revenues arrive directly?
  • damage liability: what happens if a guest causes damage? Who pays?
  • transparency on platform commissions: are these charged to you or included in the management fee?

A good property manager does not fear these questions. They expect them.

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