Why Property Management AI Feels So… Meh

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Property managers are getting flooded with AI promises right now.

Every platform is shipping something.

There are promises, demos, and dashboards with new buttons that say “smart” or “assistant.”

And every time you try one, and it disappoints, it’s tempting to think:

“I’ve seen this before. It’s not what they say it is.”

That mindset isn’t crazy. It feels like every couple of years, something comes to “disrupt” everything.  Social media, blockchain, and the metaverse have all passed through, while property management still feels just like it did when you started- exhaustingly complex and impossible to scale without breaking.

Does this sound familiar to you?

• AI features roll out and feel more “filler” than force-multiplier
• Big acquisitions come with big promises — and vanish into vague roadmaps
• You’re starting to expect less from AI… even if the rest of the world could be changed by it

You’re not imagining things. And this isn’t just a PM software problem because it’s happening everywhere.

This post nails something critical: The reason you’re not seeing the AI moment isn’t because AI is all hype. It’s because the software and partners we’ve grown to love and trust weren’t specifically built for this current environment…that really matters.

Kyle Erb, Director of Systems at Real Property Management, puts it best-

“I always tell our franchise owners that before you start using a system, you have to understand how it was intended to be used. If you try to use it in a different way, expect it to feel clunky and broken.”

It’s kinda like if you built a ship to sail to a specific destination, and the destination completely changes.

Let’s talk about that.

The Wrong Ship (And Why It Matters)

Imagine building a ship meant to cruise to a hot tropical island.

It’s going to be engineered to handle violent tropical storms.  Your crew will be prepared for tropical heat, mosquitoes, and thrive despite whatever threats this island may bring.

Then one day, the destination changes. Now you’re headed into arctic waters.  

Your ship can handle tropical storms, but can it navigate icebergs?

Are the crew’s quarters equipped to keep them warm?

Let’s say they can land and barter for warm clothes…. Do they know how to track animals and hunt on ice?

We’re not saying it’s a bad ship. We’re not questioning the ability of the crew.  But if they were built for something different, they will struggle through an adaptation process.

Because when the environment changes this much… maybe you don’t just need a different ship.

You probably need a different crew culture altogether.

A “wrong ship problem” is as much a cultural problem as it is a tooling problem.  

No one knows this type of shift better than Kyle.

Don’t Take It from Me. Take It from Someone Who’s Done It Before.

You don’t need another opinion piece about AI.

You need to hear from someone who’s been deep in the guts of this shift; who’s tested the tools; run the ops; stared down the promise of AI; tested every major tool the property management world has to offer, and felt the disappointment that followed.

That’s Kyle Erb.  He’s already led one technological transformation in property management, seen the benefits, and is even more excited about what’s coming next.

So when he talks about where things break, he’s not theorizing. He’s describing what happens in the field.

That’s why he can help us understand these underwhelming AI experiences.

Let’s start with the first thing the LinkedIn post mentioned...

The Features Sound Smart But Still Make You Do the Work

In the LinkedIn post, nails it:

“The go-to move for incumbents? Still ‘slap on a chatbot’ on top of existing data... They’re shipping safe, incremental features while startups go after full workflow automation.”

It’s what happens when AI is treated like frosting. The interface looks shinier; there’s a new button labeled “Assistant.” But underneath? It’s the same form-based logic. The system still waits for you to fill in the gaps.

Kyle Erb has seen this firsthand. And when we spoke, he offered a simple but powerful distinction that explains the letdown:

“ Having just automated templates is all outbound communication. Once it's inbound, that's where the system breaks down.”

That’s the trap: templated workflows can send tasks out. But the moment something unpredictable comes back in- a tenant responds, or a vendor asks for clarification-, the whole thing grinds to a halt.

AI vanishes.

And you’re back doing the work it promised to replace. And as Kyle puts it, you’re worse off than before the AI got introduced:

“You either have an agent or a form. Combining the two reduces the usefulness of both.”

What he’s describing isn’t just a product limitation.

It’s a “wrong ship” problem.

That means you won’t just need better tooling to succeed, you’ll need a different culture.

As Vendoroo founder, Reza Kesh, put it:

“One of the many things…on top of the technology…is having an outcome-oriented culture.”

That’s the real differentiator. It’s not picking between AI vs no AI (everyone has AI).  It’s the difference between promising tools and promising outcomes.

Most AI Teams Are Built to Underwhelm

The LinkedIn post zooms in on something that explains Why SaaS Won’t Build the Next Great AI:

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Reza Kesh, Vendoroo’s founder, explains how hard it is from a cultural standpoint:

“Culturally, you build a company for 10 years, 5 years, 20 years, that has been running away from the outcomes and building efficiency tools for property managers...
… but one of the many things on top of technology is this outcome-oriented culture that no SaaS company has.
It's actually—they've ran away from it to be able to be scalable.”

That mindset isn’t just hard to pivot from.  It shapes how the team operates, how problems are defined, and how ambitious the AI roadmap is allowed to be.

And for AI engineers inside a SaaS org, this challenge should feel familiar:

Before you can build AI that takes ownership, your leaders have to unlearn the mental scaffolding designed to avoid it.

It’s less obvious for property managers to understand they are also suffering from the externalities of the “wrong ship problem”, but they’re kind of on the same boat as AI engineers.  Pun intended.

If you’re a property manager, you don’t have to become an AI expert.

You just need to know who to listen to.

Most Advice About AI Isn’t Consciously Wrong. It’s Just Recycled.

Here’s one reason that doesn’t get talked about enough:

The majority of advice in the property management space is influenced by the captains of the “wrong ship”.

Most property managers don’t have time to research every AI development.

You lean on peers, consultants, and “tech-savvy” voices in the space to filter what matters.

But here’s the catch:
Those voices often have deep roots in the old ships.
They were raised on the same mental models.
They’ve grown up with the same partners.
That’s why they’re repeating the same assumptions, not out of malice, but momentum.

So even when they’re excited about AI…

they’re still passing along ideas that were built for a different kind of journey.  Ideas anchored on the past, not in the future.

You’ve heard AI agents “aren’t there yet” because most of them are being fit into form-based logic, and deemed underwhelming.

That’s broken logic.

AI agents need to be evaluated from an AI-first foundation.

That’s why Kyle didn’t stop searching. He knows the difference.

We’ve Been Grading AI on the Wrong Curve

There was a moment in our conversation when I had to pause.  K

yle had just nailed the expression for something I’ve been trying to explain for a long time.

That this (this whole search) wasn’t about better features. It wasn’t about smarter dashboards or cleaner forms.

It was about agency.

About finding something that doesn’t just help PMs manage the chaos, but remove it entirely.

“AI features are gimmicks. AI-first is the foundation; bolted-on AI isn’t.”

That is the shift.

And it didn’t happen because someone gave him a better demo.
It happened because he saw a completely different way to build (and realized what he’d been chasing all along).

“You start to question what you’ve accepted as normal (Maybe you’ve been accepting this too).”

That’s what Vendoroo has been doing from the start:

Designing a new kind of infrastructure for AI to actually think, act, and deliver results (not just suggest them).

An AI that isn’t bolted on, but built in.

And once you’ve seen that kind of shift…You can’t unsee it.

You stop asking “What can AI help me do?”

And start asking, “What’s possible now that I don’t have to do it all myself?"

So if everything you’ve seen so far has felt… underwhelming?

Maybe it’s time to pay more attention to the ones thinking differently from the start.

Like Kyle.

🎧 Listen to our entire conversation on the podcast→

Turns out, the right ship doesn’t just have better tools. It has a crew that thinks differently from the ground up.

Welcome aboard.

Pablo Gonzalez,

Chief Evangelist at Vendoroo

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