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AI property management is one of the buzziest terms in the industry right now. Artificial intelligence through algorithms as a concept has existed for a long time, but with the sudden virality of chatbots like ChatGPT, members of many different industries are suddenly wondering how AI will affect their business and how they can harness it. 

The same is true in property management, an industry that has already seen something of a tech revolution in the last decade. We sat down with Wolfgang Croskey, President of The Perfect Tenant, to discuss how AI will help property managers and how it could hurt them. 

If you don’t know where to start with AI, Croskey does. In this article, he breaks down the practical applications of AI in property management with us.

Key Learning Objectives:

  • What can and can’t Artificial Intelligence do for property managers?
  • How can you get the most out of AI tools?
  • What should you NOT try to do with AI?
  • What specific programs can you use right now?
  • Where is AI technology headed?

Meet the Expert: Wolfgang Croskey, President of The Perfect Tenant

Croskey has 20+ years of experience in the property management industry and is currently the President of The Perfect Tenant. Croskey is an early adopter of artificial intelligence in the property management space. Even though AI may feel like it’s in its infancy, and it technically is, there are already a number of programs that PMs can and are using to harness the power of the technology. 

What is A.I. Property Management 

AI property management is a business strategy for real estate or property management companies to streamline, simplify, and improve their processes through software automation. New technology uses machine learning and artificial intelligence to speed up workflows, day to day tasks and even help with predictive analytics and marketing tools.

In its current state, artificial intelligence can best serve property managers by streamlining administrative work. It’s calendar clearing, essentially, by giving you more time to work on your business because you have less work to do in your business. As Croskey has implemented AI solutions into his business, he’s noted how much more time his property managers have to be property managers. 

Croskey says, “Now, with the time we have, our property managers call an owner every day just saying, ‘Hey, how’s it going?’” 

Croskey’s team is able to devote more time to elements of a great resident and investor experience. It’s ironic to think that AI is helping you forge stronger relationships with clients, but it’s true. With more time to devote to opening lines of communication and being proactive in doing so, PMs can build that experience that’s the primary differentiator in modern property management. That’s what it means to work on the business. 

“Can AI replace a property manager? No. Because at the end of the day, what is a property manager hired for? To provide solutions for crazy problems. And that's what we do. But if your whole day is filled with all this admin work, how are you going to have the energy and time to solve crazy problems? Use these tools to unload as much admin stuff as possible, so you can really focus on the property manager’s true value proposition, which is solving crazy problems and helping owners make money.” 

Best A.I. Tools for Property Management 

So, how do you actually use these programs to cure your team of their grunt work pains? Let’s look at some of the top business areas and use cases for AI property management.

AI for Marketing 

With the rise of natural language processing tools like ChatGPT, creating unique marketing collateral has never been easier than it is right now. 

“If you are still wasting your time writing creative property descriptions, you just need to stop,” says Croskey. “Nobody reads them anyway. I’ll buy you lunch if you actually leased property because someone said, ‘You know what? That marketing description was phenomenal. That’s why I want to lease this house.’ Nobody has ever said that, so why would you spend a lot of time on it?” 

Croskey believes that tools like ChatGPT can spit out a perfectly viable description provided correct details of the property. He also says that a description, being something that is necessary but not critical, is a perfect candidate for time-saving via AI. 

“So the marketing and the copy is the thing you need to start right now. There's no reason not to do that. Nobody expects a property manager to be mighty in Word and to be a great writer. That's not why they come to our business. I'm not saying turn out garbage, but save time and have an AI tool like chatGPT or Jasper write the copy. Even if you don't use it 100%, it saves you a lot of time in that brainstorming.”

Beyond property descriptions, these tools are helping create blog content and other native web content for all sorts of businesses. Whether it’s long-form SEO writing for your website or short social posts, AI can give you at least a good template to work with. You should still make sure what you’re publishing represents your company as intended, but AI can get you really close to the finish line very quickly.

AI for Email 

Language processing can also help with direct communication with clients, and Croskey has leveraged the same tools for that purpose as well. 

With so much communication being templated – particularly via email – things can get stale for the readers. But regularly updating email templates and follow-up communication falls under administrative work that you’d really rather not be doing. 

“Maybe once a year, take your templates, throw them into one of these AI tools, and say, ‘Hey, can you rewrite this?’ You’re just kind of freshening up,” Croskey says. 

“You could ask it to rewrite something with a more friendly tone or add some comedy to it or different things. And so now, each year, the point of the message is the same, but you're kind of making it new and exciting. 

“I can only imagine as an owner – especially if the owner has, let's say, 10 properties, and now the odds getting those different talk trigger emails is higher – that's gotta be so boring. I mean, most people don't read their emails anyways. So you might as well have some fun with it. Maybe you say, hey, this year, we want all the templates of our emails to be in the tone of Snoop Dogg. You may laugh, but you could do that, right?”

AI for Scheduling 

Croskey has also leveraged AI tools for more robust management of his work calendars, maintenance requests, onboarding, etc. Most people have a scheduling app, but Croskey has started a real-time AI tool to go a step further. 

“The biggest problem with any basic scheduling app is the concept of priority, right? Apps without AI integrations simply look at free and busy times. For example: ‘Oh, this person wants 30 minutes. Let me find the next open spot for 30 minutes and plug them in there.’ But let's say you wanted an hour with me. If I didn't manually intervene, you probably wouldn't be able to get the hour for like two weeks because finding an hour-long spot is not going to happen. But I want to give you priority, so I had to override my account and say you know what, let's do 8 am.”

To solve this, Croskey has enlisted a tool called Reclaim.ai that’s designed to make scheduling decisions based on priority instead of just available time slots. We’ll talk more about it in the next section.

Property Management AI Programs to Know

Croskey has used a number of AI programs to help with administrative and communications work. He goes into detail about each of them here. 

Chat GPT and Jasper

Chat GPT is a natural language processing tool publicly available at openai.com. It will write things for you while including whatever tone, keywords, structure, concepts, etc., you ask it to. 

One of the drawbacks of ChatGPT (free version) is its limit on a concurrent number of users. You can’t use it if too many other people are currently using it. Jasper is a paid alternative that relieves you of this issue, and a paid version of ChatGPT now exists as well.  


Croskey says:

“The other tool is Grammarly,” Croskey says. “Grammarly on the paid level is a game changer. Because what you can do, as a company, you can establish the tone of communication for your company. Do you want it super serious and academic? Do you want it funny, more casual? You can create all those rules, and then as you're writing, Grammarly integrates itself into your web browser. Whether you're using Google Docs or LeadSimple or Asana, or anything else, it's in there. You can have it on your mobile device, too. 

“So anywhere you're writing, it’s making suggestions not just to make it grammatically correct but ‘Hey, this message may be interpreted as being too serious.’ Or ‘This message may be interpreted as being too direct.’ That's huge.”


Reclaim.ai is a smarter scheduling app. 

According to Croskey: “Reclaim.ai is smart scheduling because it does the traditional scheduling, but then it has the ability to help you with your habits.”

“If you, for example, want to have a 30-minute lunch every day, you can go ahead and do that. And what it will do is it will find 30-minute chunks, but if an appointment comes in that you say is more important by using some rules, it will then move it around for you. So you can put in habits, but now they just released the ability for priority. 

“You can have different scheduling links, and so I have a high-priority one. If [a client] wants to meet with high priority, he gets a different link, and [reclaim.ai] will say ‘anything from this link trumps everything else,’ and it will start moving things around to give them the priority.”

“Let's say you use Google task lists, you can have it automatically go in there. So you say this task needs to be done by the 23rd, and I need 30 minutes. It finds the task, and as things trump it, it will move it around, but eventually, it gets to the point where it says, ‘You know what, you're out of moving time, this is stuck now in order for you to hit this deadline.”

What You Shouldn’t Automate with Artificial Intelligence  

While AI can solve tons of issues and make work better, there are still functions that are better accomplished by a human being. 

Think about it this way: Have you ever used a power drill? It’s a pretty useful tool. If you measure correctly, mark your holes cleanly and accurately, use the right screw, and apply the right amount of pressure, a power drill will help you hang something on the wall. But if you just throw your drill at the wall and hope for the best, it will only leave you with a beat-up wall. 

This is a story about artificial intelligence. AI is a tool. It’s not a magic bean. If used incorrectly, AI can do more harm than good. Here are two common pitfalls of over-dependence on AI.

Creating Business Policies and Procedures

Croskey says: “The reality is that if you don’t have your policies and your procedures, there is no tool on earth that is going to save your bacon. You gotta roll up your sleeves, and you gotta get through that. Look at McDonald’s. At one point, somebody had to roll up their sleeves and make the process of how to build the Big Mac. It probably took quite a while to do that, but now that it’s done, they haven’t changed the Big Mac for at least 40 years. It’s still the same nasty hamburger.” 

Property management AI can help you repeat your processes, but it can’t create them for you, and it can streamline them, but it can’t optimize them for success. 

For example, say you’re writing a blog post for your website. You still need to do your research on what topics create the best opportunities for you to generate organic website traffic. You still have to decide what stance, if any, you’re taking on the subject. You still have to decide what tone you want your content to take. This is the information that can then be fed to AI to rapidly create the content. But the macro decision-making still has to be you. 

That’s the single biggest mistake you can make here, expecting the tool to use itself. 

Overreliance on technology is kind of an innate vulnerability with tools so robust. Croskey is quick to clarify that such a mistake can lead to notification overload, where you can’t keep up with everything that all these tech tools are delivering to you. You still have to be aware of what’s going on in your business. 

Training Personnel

The veteran PM also notes that, just like with any new tech, proper training for the team is of critical importance. 

“Really do your team justice by providing them training, providing them opportunities, not just saying, ‘Okay, starting tomorrow, we're using Jasper, have a nice day.’ Really do some training.”

For training, Croskey recommends the non-AI tech tool, Loom. You can create screen recordings and build a library of training materials for your team. 

“Loom does provide transcripts of the videos, too,” Croskey says. “You could take those transcripts and say, ‘Hey, chatGPT, Could you write me a summary of this?’ And it will do it. So now you can put that summary in your email.”

A big part of AI implementation is understanding what’s actually happening. This may seem tedious and unnecessary, but people leave companies for less. You can’t just have one person in charge of AI with everybody else completely unaware of how it’s working for the business. Croskey likened this scenario to one employee holding bank login info and then leaving the company. It’s a headache that can be avoided with solid education of the team. 

Future of A.I. in Property Management: Where Does AI Go Next?

As of now, the strategies above outline how Croskey and other PMs are finding value in artificial intelligence. AI will continue to evolve, and the technology is going to build advancements more for PMs in the future, especially with integrations with property management software.

“Right now, all the AI is around language because I think it’s probably easier,” Croskey says. “I think the next step is going to be the math and numbers side, being able to look at your numbers, your portfolio, your financials, and start making recommendations from that.”

Croskey predicts that AI could aid in ROI analysis and decision-making, essentially doing analytics of data points associated with specific properties and identifying trends and associations within your portfolio that can help you increase the profitability of your doors. 

The last place you’ll see AI reach, according to Croskey, is the maintenance realm.

“There's a reason why nobody has really fully nailed down maintenance,” he says. “There are just so many variables and one-off things that it's hard to get a machine to learn that. For example, work orders come in, and the tenant says, ‘Oh, my toilet is leaking.’ Well, is it leaking from the floor? Is it leaking underneath? Is it just running? So there are three variables right there. Is it a low-flow toilet? Is it not a low-flow toilet? There are variables there. There are just all these things that can be going on that make maintenance hard. So I think that maintenance is going to be later in life.”

Final Thoughts 

AI property management tools are nothing to be afraid of and can be a massive support to streamlining business processes, workflows, and day-to-day operations. Many leaders in property management are already leveraging AI apps and products to make their work better.

The true benefit of AI is that it can automate busy work and repetitive tasks – freeing you up to be strategic, focus on relationships, and build better resident experiences. AI tools help PMCs keep up and compete with commoditization, as well.

Follow us on LinkedIn, Twitter, or Facebook to stay up to date on these AI conversations. We’ll keep the conversation going and continue to deliver the best insights from experts across the industry.

Hear more from Wolfgang Croskey and other PMs who have used AI on the Triple Win Property Management podcast.