Is Property Management Difficult? by Taran Hughes

A Straight Answer (From Someone Who’s Seen Both Sides)

Short answer? Yes. No. Well… it depends.

And that’s not fence-sitting. It’s the most honest answer you can give.

Because “property management” is never just one thing. If you already own property, you’ll know exactly what that means. One minute you’re chasing a contractor who’s gone suspiciously quiet. The next, you’re onboarding a tenant, juggling finances, dealing with certificates, fielding questions, and keeping one eye on whatever new regulation the government has decided to introduce this month.

Somewhere in the middle of all that, you were meant to be growing your portfolio, or at least enjoying a quiet weekend. Instead, property management has taken up residence in your head—rent-free.

When Property Management Starts to Feel Hard

If you’ve got one or two properties, you can usually keep things under control. You remember most deadlines. You know your tenants. You can firefight when something pops up. But scale even slightly, and the complexity multiplies fast. Suddenly you’re managing:

• tenants
• contractors
• inspections
• safety certificates
• renewals
• compliance deadlines

Each one has consequences if it’s missed. And it often starts with something small.

• The gas certificate expires.
• The move-in date slips.
• The tenant gets frustrated.
• The whole timeline unravels.

That’s usually the moment people decide property management is “a nightmare”.

The Real Problem Isn’t Property Management

It’s How It’s Done. Property management isn’t inherently difficult. It becomes difficult when it’s:

• reactive
• disorganised
• stored mainly in your head

And no—Post-it notes are not a system. When everything lives in your memory (or scattered across emails, texts, and spreadsheets), you’re constantly second-guessing yourself:

• “Did I do that already?”
• “Was that certificate renewed?”
• “Did I reply to that tenant… or just think about it?”

That mental load is what makes property management exhausting. Done properly, it looks very different.

From Firefighting to Flying the Plane

Well-run property management doesn’t feel frantic. It feels controlled. The best analogy is a cockpit. You’re not flapping around mid-air trying to remember which lever does what. You’re calm because the instruments are telling you what’s happening.

• Properties stay full
• Tenants know where to go
• Issues are logged, tracked, and resolved
• Compliance happens on time

And crucially, your weekends come back. So how do you get there?

The Two Levers That Change Everything

There are two things that separate stressed landlords from calm ones: systems and people.

1. Systems: Stop Running Your Portfolio in Your Head

The SaaS and PropTech world has transformed property management. Instead of juggling spreadsheets, inboxes, and reminders, purpose-built platforms now do the heavy lifting. Tools like:

• COHO for HMO and portfolio management in a single dashboard
• Xero or LettsPay for clean, automated accounting
• Help Me Fix for maintenance triage and issue tracking

These systems turn chaos into visibility. You can see what’s happening, what’s overdue, and what needs attention—without constantly chasing yourself. Once everything is logged and centralised, management becomes proactive instead of reactive.

2. People: Your Back Office Doesn’t Need to Sit Next to You

The second shift is people. Thanks to technology, your “back office” doesn’t need to be in your office or even in your country. It might be someone local. It might be someone 6,000 miles away. What matters is that they’re trained, consistent, and supported by the right systems. The right team can:

• handle admin
• manage compliance checks
• deal with tenant communication
• log maintenance and follow-ups

That frees you up to focus on growth—or simply enjoy a quieter life. When systems and people work together, property management stops being something you survive and starts being something you run.

So… Is Property Management Difficult?

Yes, if you:

• try to do everything yourself
• keep it all in your head
• wing it day by day

But no, not if you treat it like a business. With structure, the right tools, and the right support, property management becomes predictable. Boring, even in the best possible way. The late-night “Did I forget something?” moments disappear. The constant low-level stress fades. And what’s left is a system that works for you, your tenants, and your long-term goals.

So is property management difficult? Only if you try to do it alone.