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How to Choose a Property Management Company: Lessons from the Field

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When I started investing in real estate 15 years ago while living overseas, I had a very simple picture in my mind of what a property manager (PM) should do:

Collect rent; Maintain friendly communication with tenants; Handle repairs like they would on their own home; Manage tenant turnover smoothly
End of story, right? Not quite.

End of story, right? Not quite.

Back then, I had no idea how much variation there could be between property management companies — or how critical the right partnership would be to the success (or failure) of my investments.

Some of the property managers I started with in other markets are still with me today. But when I entered the Philadelphia rental market eight years ago, I had a rude awakening. The first PMs I hired in Philly didn’t just fail to meet my expectations — they actively cost me money. Miscommunication, lack of transparency, slow response times, poor vendor management… you name it.

That experience forced me to get clear on what really matters when choosing a property manager. Here’s what I learned — and what I recommend everyone working with a PM should look for.

1. Read the Management Agreement Carefully

If it’s not in the agreement, it’s not part of the deal. Don’t assume anything.

✅ Want regular inspections with photos? Put it in writing.
✅ Expect owner draws by the 10th of each month? Make sure it’s spelled out.
✅ Want detailed financial reports? Confirm the frequency and format.

The contract is the foundation of your relationship. Get granular. Ask questions. And don’t sign until everything you care about is included.

2. Clarify How Vacant Units Are Handled

Some PMs continue to charge fees even when a unit is sitting empty. Make sure you know:

  • Will you be billed during vacancy?

  • What, if anything, are they doing during that time (e.g., marketing, repairs, updates)?

  • Are there renewal or lease-up fees?

3. Ask About Communication Standards

This one is huge.

  • How quickly do they respond to emails?

  • Is there a dedicated contact person for your properties?

  • Will you be notified of tenant issues or maintenance requests in real-time?

A good PM communicates clearly, consistently, and proactively.

4. Understand Their Maintenance Protocols

This is where things often fall apart — and where costs can spiral.

Here’s what I insist on in Philly:

  • I must be notified immediately of any maintenance issue

  • I can provide my own vendors

  • I can request multiple estimates

  • I receive photos and documentation of the issue

  • I can speak to the tenant directly if needed

If a PM resists transparency or tries to cut you out of the process, that’s a red flag. Maintenance is where a lot of your money gets spent — stay involved. Not to mention that the property is YOUR asset – you need to know what is happening and maintain records. Each repair involves multiple decisions and those decisions should be yours to make.

5. Discuss Late Payments and Evictions

Every company handles this differently.

Some are proactive and personally engage with late-paying tenants. Others go straight to eviction with no effort to retain. And some do… nothing.

You need to know:

  • What is their late fee policy?

  • When do they contact tenants about late rent?

  • Do they offer payment plans?

  • When do they start legal proceedings — and how do they handle the eviction process?

This is a major area where bad management can lead to bigger losses than you expect.

6. Define Roles and Responsibilities

Even with a great PM, you may still be on the hook for some tasks. Discuss in advance what they handle vs. what’s still your job. A strong property manager won’t try to read your mind — but they will support your business if the roles are clearly defined.

The Bottom Line

Property management can be a game-changer — in both directions.

A poorly run company can destroy your cash flow and add stress. A great one can become a trusted partner, helping you scale efficiently and protect your investments.

Look for:

  • Defined processes

  • Experienced, trained staff

  • Clear communication

  • Flexibility to match your preferences

  • And above all, transparency

Ask the hard questions upfront. And if something doesn’t feel right — keep looking.

Want to talk more about finding or vetting property managers in Philly? I’m always happy to share what I’ve learned. Just reach out.

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