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Whether you’re a board member of a self-managed community association or a property manager overseeing multiple associations, property management software can transform how you work. 85% of property managers already rely on software to streamline their operations. But with so many options, how do you choose the right one?

We’ve compiled insights from experienced association managers to uncover the five most critical questions to ask before investing in property management software. These tips will guide you to the perfect solution.

1. What Part of Your Job Causes the Most Stress?

The best software solves your biggest pain points. Start by listing daily challenges, such as:

  • Manual payment processing

  • Time-consuming communication with residents

  • Tracking maintenance requests

  • Generating financial reports

Involve your staff to get a complete picture, then match these challenges to software features.

How Software Helps:

  • Automates recurring EFTs for association dues, processing millions monthly without manual banking.

  • Streamlines multiple routines with features like global search for instant access to information, speeding up task completion.

2. What Do Your Association Board & Owners Need?

Your software should simplify life for board members and residents, who use it for tasks like paying dues, submitting maintenance tickets, or accessing reports. Survey your community to understand their needs, focusing on:

  • Mobile app access

  • Report visibility

  • Meeting notes and voting processes

  • Training support

How Software Helps:

  • Offers a task system for residents to submit requests, keeping inboxes clear and tracking progress.

  • Enables portfolio-wide announcements via eblast features and instant file uploads for homeowner access.

3. What Kind of Data and Report Access Do You Need?

Property management often takes you out of the office, so cloud-based software (SaaS) is essential for real-time access to data and reports. Benefits include:

  • Mobile Access: View documents uploaded by staff instantly.

  • Team Logins: No licensing limits—everyone can access the platform.

  • Automatic Updates: No manual updates or restarts.

  • Data Security: Redundant backups protect your files.

Solutions like HomeWiseDocs also help manage documentation for property sales or refinancing, ensuring compliance and even generating revenue.

How Software Helps:

  • Prioritizes good data exports, device accessibility, and reliable uptime.

  • Offers intuitive interfaces with strong support systems that residents can navigate easily.

4. How Will You Communicate with Stakeholders?

Communication preferences vary, so pick software that aligns with yours while being user-friendly for board members, residents, vendors, and staff. Avoid tools that clutter your inbox or force phone calls if those aren’t your style. Look for software that:

  • Streamlines communication

  • Saves time

  • Reduces stress

How Software Helps:

  • Converts email requests into trackable tasks, ensuring nothing gets buried and maintaining accountability.

  • Saves front offices 5–10 hours weekly, accounting teams 15 hours monthly, and property managers at least an hour daily.

5. Will Your Software Scale with Your Business?

As your portfolio grows, your software must keep up. Consider:

  • Payment Processing: Manual payments become overwhelming with more units.

  • Communication Load: More stakeholders mean more messages.

  • Tax Complexity: Software should simplify 1099 processing.

  • Staff Training: Ensure the platform is easy to learn.

The right software saves time now and supports future growth.

How Software Helps:

  • Scales effortlessly with automated EFTs and task systems for growing portfolios.

  • Streamlines operations and intuitive design make onboarding new units and staff seamless.

Conclusion

Choosing the right property management software starts with understanding your needs, your community’s expectations, and your growth goals. By asking these five questions—about stress points, stakeholder needs, data access, communication, and scalability—you’ll find a solution that saves time, reduces stress, and scales with your business.

Ready to explore? Survey your team and community, evaluate features against your challenges, and invest in software that empowers your association management.