Top 10 Questions to Ask Before Choosing a Property Management System

Being a property manager (PM) can often feel like being a jack of all trades (and occasionally a master of none).
The job is a hybrid one, and PMs must don many hats, from revenue manager to photographer, booking agent, and even occasional have-a-go plumber.

But the fast-moving world of technology, and the seismic impact it’s making across the broader hospitality sector, means PMs must also fill the shoes of software experts. Today, it is essential for PMs of all sizes to be using a robust property management system.

These help streamline operations, centralise bookings, and enhance overall efficiency. 

However, the sheer volume of options available can be overwhelming, even for the most tech-savvy managers. To navigate what can feel like a labyrinth of choice and find the perfect system for your needs, it’s important to know what you should be looking for in the first place.
So, here are the top 10 questions every property manager should ask before picking a PMS:

1. What features are integrated into your software?

Knowing what features are integrated will help you assess if the software can meet your business needs. For example, if your booking engine and payment processing tools are integrated, you’ll be able to accept bookings and payments far more seamlessly. Likewise, integrations also ensure that both direct and OTA (Online Travel Agency) bookings appear in one unified booking calendar. Simply put, more integration means fewer complications.

Look for: A comprehensive list of features encompassing booking management, channel management, guest communication, payment processing, reporting capabilities and automation tools. Ensure the software covers all critical aspects of your operations to reduce the need for multiple systems.

2. Do you connect to my preferred channels?

The PMS should integrate seamlessly with the booking channels where your properties are listed.

Look for: Deep API integrations with major OTAs like Airbnb, Booking.com, Vrbo, and Expedia are crucial. You want the PMS to have real-time synchronisation of rates and availability across channels. The best channel managers also automatically sync other elements such as policies, content, and photos across your channels, saving countless hours on manual updates to OTA extranets. And with OTAs frequently rolling out updates to their APIs, it is essential that your PMS is capable of automatically adapting to all these changes, too.

3. What is your customer service like?

Good customer support is vital for minimising downtime.

Look for: 24/7 support, multiple contact methods (phone, email, chat), and additional resources like training materials, FAQs, and webinars. High ratings on review platforms like Trustpilot or Capterra indicate strong customer service.

4. Do you have extra features for next-level vacation rental management?

These set apart the good from the great. As you scale, these features can help you quickly manage an increase in guest bookings and all the work that comes with it.

Look for: Guest engagement, dynamic pricing, and report writing features. Guest experience is a key differentiator in vacation rentals, so extra features like an AI-powered messaging tool to address guest enquiries, a unified inbox, and reviews automation can prove valuable. A software that can generate thorough reports around your KPIs will help you assess performance. And an automated dynamic pricing tool will save you a lot of time updating rates.

5. How much does it cost?

Understanding the cost structure helps you budget appropriately and avoid unexpected expenses.

Look for: Clear pricing models (monthly or annual subscriptions), any additional fees (transaction fees, setup fees), and what each pricing tier includes. Ensure there are no hidden costs and that the software offers good value for money.

6. Are you a ‘multi-everything’ platform?

A versatile platform that supports multiple devices, users, channels, and properties is crucial for efficient management, especially if you’re managing properties remotely.

Look for: Multi-device compatibility (desktop, tablet, mobile), multi-user access with user- and role-based permissions, multi-channel integration, and features that support multi-property management, such as bulk updates and centralised dashboards. Bonus points if it comes with a powerful mobile app to help you manage properties on the go.

7. How secure is your payment processing?

Security is critical to protect your business and your guests’ sensitive information.

Look for: Level 1 PCI compliance, secure payment gateways, and features that automate payment collection while ensuring data protection. Transparency about their security measures and regular updates to security protocols are essential.

8. What third-party integrations are available?

Seamless integration with other tools enhances your operations and allows for better data management.

Look for: Integrations with tools such as contactless check-in solutions, accounting software, dynamic pricing tools, guest management systems, insurance providers, and cleaning and maintenance scheduling tools. The ability to connect with popular apps through platforms like Zapier will be a significant advantage.

9. What do you offer outside of your software?

Additional resources and support can enhance your experience and help you maximise the software’s potential.

Look for: Educational resources, industry trend insights and marketing support. Programs that help you get free media coverage can be hugely beneficial for exposure.

10. Is your software scalable?

The software must be scalable not just in terms of managing multiple properties but also in handling different types of properties. It’s essential for the system to be an all-in-one solution for hybrid operators, such as those managing both vacation rentals and hotels, or adopting a hybrid rental model (e.g. selling a vacation rental property as one unit in the summer and individual rooms in the winter.)

Look for: Cloud-based solutions that offer scalability with features designed for large portfolios, encompassing the ability to add new properties and users without significant additional costs. If you’re a hybrid operator, look for features that meet your specific needs, like the ability to set different pricing, tax and automation for your different property types. Find testimonials from users who have successfully scaled their businesses using the software. Great to have: multi-property views and bulk management tools, owner management features, a cleaning and maintenance dashboard. Bonus points if it comes with a template for a multi-property website.

Choosing the right PMS is critical for your efficiency and growth. By asking the right questions, you can choose the best system that meets your specific needs, integrates seamlessly with your operations, and provides the support and scalability required for long-term success.