When does self-managing stop making sense?

It’s all about the math for us.  Self managing makes the numbers for STR work as most PM are expensive and do a comparably poorer job. Maybe if people bought property when interest rates were 3% the numbers still cover a PM but not now. Plus it earns hours for material participation and bonus depreciation now that that’s back. Not sure what the number is but perhaps if you had enough properties in one location to get enough of a discount on PM it would make more sense.

We started a few years with one property and inherited the “mom and pop” management company that was handing things for the prior owners (it’s a shore town… it was one of the legacy “been around for 50 years” type of places).

We ended things with them pretty quickly… they used fixed rate sheets, they only rented by the week or “mini-week”, their knowledge of the major OTAs was lacking (outsourced to a “tech guy”), and their in-house cleaners weren’t even that great.

So we ditched them, in favor of Evolve. We liked their hybrid model… they are not “boots on the ground” but they handle all the channel management and revenue management. We were happy for a while and were actually pretty proud of how we were doing compared to the prior owners.

Over time though, and by the time we bought our 3rd property, Evolve’s value proposition diminished greatly. “Why are we paying them so much, when WE’RE doing most of the work anyway?” Most frustrating of all was the unnecessary layer between us and the guests when it came to communication.

As a highly technical person (ex-Microsoft employee), it didn’t seem hard to do what Evolve was doing. And we were right. As soon as we launched our 3rd property, we were running circles around Evolve and KILLING IT on rates and occupancy compared to them. We started feeling sick at how much money we had given them over the years, for what was really just a little bit of up-front effort -- “set it and forget it.”

As we on-boarded our 4th property, we told Evolve to stop taking reservations on our first 2. We were self-managing #3 and #4 pretty well without needing a PMS… just making sure that Airbnb and Vrbo and BDC were staying in sync and only being slightly inconvenienced by having to log into each OTA separately to make changes.

But when it came time to fire Evolve and bring our first two properties into the self-management fold (for a total of 4), that’s when we started evaluating PMSs and landed on Hospitable. Very happy with that decision, as it also finally solved the problem of repeat guests wanting a direct booking option. And now it’s opened up the possibility of starting to co-host or manage for others, which is definitely in the realm of possibility for the near future.   

Great points ​@EricMiller! And sadly, there are so many who don’t know about bonus depreciation. Do you also maintain a full time W2 job, while self-managing? 

​@Tom Beerley Love your story! We’re working on something pretty special that we hope will help customers like you nail their first owner and begin managing for others. I’d love to hear… how are you thinking about taking on your fist management client? What gaps are present today that you feel you need to fill before you’d be ready? And when you start searching for opportunities, how you assess whether a property is a good fit or not? (If you want to chat about this 1:1you’re welcome to book something with me here.)

​@Emily Tunggala I’m fortunate to have a relative who owns a condo in the same building as one of ours. She recently decided to start renting her place out, and was happy to be my first client. So I have a very patient and forgiving first client to cut my teeth on. I couldn’t fathom having a stranger as my first client… It would be way too obvious that I’m figuring things out as I go (not operationally… just in regard to “managing for others.”).

So the main gaps for me to fill right now are all the things involved with having an arms-length, paying client. What to charge, how to formalize the agreement, how often to do payouts, how to handle up-front investments needed to bring a property up to our standards, whether to list third-party properties under the same account as our own properties (risky given our nothing-but-5-stars track record). And 100 other similar questions. 

Basically I need a PM 101 course LOL. I greatly admire the folks in these forums that are operating at a good scale already. I already know that operationally speaking, I could scale to 100 properties if I owned them all. It’s building out a mature-looking set of SOPs for client-owned properties that will be the biggest challenge. 

I’ll definitely book some time with you to get more of your thoughts. Thank you for that! 

I’ve self-managed long-term and short-term rentals. I’ve done so from the other side of the country and locally. I also have an accounting and tax background. I think there is no value that can be placed on the amount of experience I’ve gained self-managing. That more than anything is why I chose to self-manage. Sure, there are instances where my time might be better spent elsewhere in the business/life. Every time I look into PMs they wants anywhere from 8-12% to basically process rent. Some require you to use prescribed vendors, some get kick-backs/referral fees/commissions. I’ve actually had a top rated PM in my area refuse to take on a challenging property because it would be “too much work”.

Ultimately, I’ve built a great local network of vendors and professionals, it took quite a while and I did have to kiss some frogs along the way. I also do get 3 quotes for everything which helps me identify which vendors to avoid more than which ones to build a relationship with. I am also quick to stop using a vendor. 

What makes self-managing worth it is the experience/knowledge gained and having that experience/knowledge to know when something is not a DIY matter. When is a PM worth it? In my experience very rarely (especially at these cap rates). I’d rather build that capability in house (when scaling). Especially for labor/maintenance services I just need someone to continue to manage those relationships. For accounting/tax matters I’m my own resource. For legal matters I seek out attorneys in the respective niche. I think 4-5 years in the flywheel started to catch a bit of momentum and I was getting referred to top tier professionals. I wouldn’t have been able to make any of these connections without self-managing. 

Caveat being that I am a small operator with a handful of doors. Not every business needs to scale to be profitable. 

What I need is a sophisticated portal and intuitive UI to serve as a hub for my residents, employees, and partners. Especially as a small operator I need something that can layer over my business without trying to pull me away from my business and into the platform. Popular ones have continued to be bought up. 

• cheap rent processing (MVP)
• Applications (MVP)
• maintenance requests (MVP)
• simple investor relations (dashboard, real-time reporting, etc.)
• calendar scheduling for inspections and maintenance 
• services upsells (landscaping, grounds maintenance, cleaners, etc.)

I have been using this software for over a year and it has significantly streamlined my operations. However, I have recently encountered some technical discrepancies regarding pricing and Vrbo synchronization. I have already contacted the support team and am currently awaiting a resolution. Has anyone else in the community experienced similar issues recently?

I have been a property manager for nearly six years, currently overseeing three of my own properties and managing four additional units for other owners. I really love it and look forward to taking on more properties, but not until this VRBO issue is fixed once and for all. I’ve tried manual resyncing...and connecting it again. It almost caused double bookings. 

I know the sample size is small so far, but it’s interesting that there’s a strong leaning toward “self-management is THE WAY” and “I would NEVER trust someone else to do what I’m doing.” As opposed to “here’s what made me decide to STOP self-managing.” But yet Hospitable is investing in building a Property Manager Marketplace, based on demand that they have already gauged, and I think it’s a great opportunity to extend my self-management expertise to folks who WANT or NEED someone to handle things for them. It seems there IS a strong demand for this. Those people are just not participants in this forum… because they’re at a 9-to-5 job, or whatever :-)

Love reading the contributions here!  Solid thinkers are in this chat :) 

As far as I can make sense of it the decision on whether to self manage and where you go from there depends heavily on personality and vision. 

On my personal journey I grew a self-managed rental property portfolio and was deeply encouraging and I felt like a boss in every way and in most rooms I was in I was treated that way.  It felt very nice.

Then one day I went down a little math road and ended up calculating that the ROI on my time spent in managing my rental properties was just under $2/hour.  That day of math forever changed the “boss mode” feeling I had as it quickly rubbed up against my hourly potential in . . . EVERYTHING ELSE!

Then come to realize out that when somebody is good at something and they try then they actually get more than 1 widget out of the 1 hour they put in.  They in fact get a better return PER hour than I would be getting, and I would get a better return per hour that I put in elsewhere.  I know . . . simple stuff, but profoundly impactful for my journey.

Turns out THE RIGHT partners are a sort of rocket fuel in your journey and you can go to the moon and back in most roles, but your odds of true, lasting success without partners (and I mean partners in the sense of people walking alongside you in a contributive way, not necessarily business partners) is quite a bit lower. 

So, to self-manage, spin up into a PM company, or hire a 3rd party manager and deploy your time elsewhere . . . whatever route you choose approach it with an excellence focus and do it like a sage pro would, then look to surround yourself with partner-level people, ideally who rock at things you stink at. 

Them’s my 2 cents, for what their worth 🤓

We just hired a full time VA in the Philippines who is a former Airbnb employee (so can deal with Airbnb and sticky situations even better than we can) and came from managing 61 rentals in San Diego.  It’s extremely affordable. Highly recommend this approach in place of a property manager + your strong team of cleaners and repair people. This is what folks in our business coaching group are doing and there is a network of VAs who are former Airbnb employees looking for jobs. 

​@Emily Tunggala - you ask a very thought-provoking question. The answer as you can see in the thread is very different for many people. For us, right now, managing our properties and excelling at operations hospitality are exciting and fulfilling. 
 

More automation and artificial intelligence has allowed us to stretch beyond what manual tasks would have held us back on. 
 

When we think about much further out in the future, and not spending as much time on this business, it may make more sense to handover the reigns to a trusted property manager. Of course we know there would be the trading money for time equation at play. 
 

As we consider bringing more properties on to grow, develop and scale were thankful to have Hospitable support us along this journey. 

I've been landlording since 2000 and self-managing successfully for years. In 2021 I rehabbed a 2-1 and got started with STR. In 2022, I began managing for others and have since grown to 11 listings via the Airbnb co-host platform.

With my background as a real estate mentor, I focus heavily on the numbers. I charge 20% (using Hospitable/PriceLabs) and the ROI for my owners consistently beats long-term leasing.

Is a PM too expensive? It depends on how you value your time. I paid $90 for an oil change yesterday. I can do it myself, but in 2-degree weather, I'd rather pay a pro and buy back my time. Not everyone is cut out to be a host, and that is where a good PM adds value.

Don't let interest rates scare you off—my goal is to buy more this year by thinking outside the box.

I agree with ​@EricMiller, you only hire a PM as a last resort

This is a fascinating topic, and one we’ve had a front-row seat to. We’ve seen many friends enter short-term rentals after watching our journey, viewing it as a clear path to wealth creation. On paper, managing one property seemed manageable. In reality, about a year in, the friction set in—guest communication, coordinating contractors, and the constant operational interruptions. What started as an “investment” began to feel like a second job.

That’s when many of them turned to us for management. Our business didn’t grow through marketing—it grew organically through experience. Today, those same owners are focused less on day-to-day operations and more on what actually compounds wealth: acquiring their next asset. We handle the execution.

Everyone’s path is different, but based on what we’ve consistently observed, self-managing one or two properties often doesn’t make sense for high-performing W-2 professionals. Time, attention, and mental bandwidth are finite resources. When those are already stretched, operational efficiency matters more than headline management fees.

We see the same pattern across short-term, mid-term, and long-term rentals. In many cases, professional management allows us to optimize pricing, reduce vacancy, and improve operational consistency to the point where owners’ take-home income remains very close to—or even exceeds—what they earned while self-managing. The difference is that they get their time back.

The real unlock isn’t doing everything yourself. It’s building systems that let you scale without burning out.

We had our back against the wall and started off with hiring a PM.  Over time we (7 months) and our property that we invested $400k into was barely performing. A few bookings and a few bad reviews. We fired our PM and took over self managing and turned a new corner. Within a year we became the top property in the area, and then it sparked interest from other owner operators. We were given the opportunity to manage for another local owner and now 2 ½ years later we are the top preferred management company in St. Augustine, FL. We took a bad situation and turned it into a positive. By speaking with so many owners, our story is common. People pour their hard earned income into an investment and it just doesn't perform. Management could be a key performing indicator of why that is among many other reasons. 

Well said, ​@Will.Fraser !  Self-managing my sole property makes the most sense financially (someone else mentioned high interest rates- we purchased ours within the past year- AND our HOA charges $100 per rental.  Yup, ouch.  I wouldn’t even break even let alone make any profit if I had to pay a manager.

But honestly, bigger than financially, self-managing does come down to that personality piece.  To give a little background, I spent 15 years as a high school and middle school classroom teacher.  I enjoyed classroom teaching very much but the ROI for the endless hours of creativity I put into my lesson plans, extracurriculars for the kids, trips abroad (I was a French teacher) just did not match up with my teaching salary.  I was always getting better and better at my job with nothing to show for it in financial terms (unfortunatley Ameríca’s favorite success metric!)  Throughout my teaching career, I had always had some form of real estate as a side hustle: I turned my first home into a long term rental, then a room in my primary home into an STR, and now I own my first property that operates almost entirely as an STR (we use it a few days a year).  

With the huge tax advantages of self-managing, it makes more sense for me to self-manage to offset small W2 jobs I have (I still work part time for an online school & teach adult night classes).  It’s the best of both worlds: I can continue teaching and now do it for the love of the craft knowing that I have other streams of income coming in with my STR.

The freedom to make my own schedule versus being tied to the school calendar is priceless. I can work a 12 hour day, then take a day off to go skiing, take a last minute trip to visit family.  I could run numbers all day and hem and haw over whether I’d be making a little more still teaching at maybe a better district, but is 10k more salary really worth more than your total freedom to be your own boss and craft each day as a new day?  I have asked myself this question every tax period for the last three years now and the answer keeps being now. The teaching jobs will always be there.

Again, back to Will’s point about personality: my lifestyle would drive a routine-based person bonkers.  For someone like myself though who has always been a creative person and has been really bored to tears by 9 to 5’s, self-management is a great fit.

​@Charles Island What’s the quality of leads like on Anrbnb’s co-host platform? How much time do you dedicate towards vetting incoming opportunities from Airbnb? We’ve heard mixed feedback from our customers on whether or not participating in the co-host platform is a net positive once they’ve reached a certain level. Curious what your experience has been?

​@ChillHolidayZ You make such great points! I’ve highlighted a few that we’ve also observed. When we’ve spoken with owners who are considering hiring a property manager, often we’re hearing that they’re focusing their time and money on acquiring their next property. The assumption out there is that owners looking to hire a PM need help because they can’t figure it out themselves (maybe they’re not tech savvy, or are just overwhelmed by all that it entails) but in reality, they can and they simply choose to focus their efforts on things that bring them more wealth. Honestly, this type of owner is probably the best type of client to have, because they’re constantly bringing you more business as they acquire more properties.

​@Emily Tunggala 

The quality of leads from the Airbnb co-host platform has actually been fantastic for me. It’s been a primary driver in connecting me with many of the owners I work with today.

To manage the volume and ensure quality, I’ve developed a specific funnel that all incoming leads go through. This helps me qualify them quickly and determine if our management style is a good fit for their goals. If they successfully make it through that vetting process, they are directed to a service menu where they can select their desired package and receive the contract automatically.

For anyone looking to grow their management business, I’d definitely suggest staying on the platform—the exposure is hard to beat.

I’ve also recorded a quick video response with more details here: https://vid.us/7r2b08

We actually started back in 2018 after struggling to find a well-done short-term rental in Joshua Tree (believe it or not, there were only about 200 listings at the time). Shortly after, a death in the family forced a career change — and with a 2-year-old at home and another on the way, I decided life was too short not to go all-in on something I truly believed in (and that would give us flexibility with our kids).

We purchased our first property and, true to form, I went deep into research mode and began building systems for everything: pricing, guest experience, turnovers, maintenance, and operations. That property quickly gained traction and was even featured in Architectural Digest, which gave us the confidence to purchase our second.

Not long after, a friend of a friend asked if I’d manage her home after seeing our results — and that’s when it clicked. We had already built the infrastructure, workflows, and standards for ourselves as owners. It felt limiting to keep that to just one or two properties. So we decided to co-host for others — but do it the way we would want it done as owners first.

Today, my husband and I both work full time in the business. We’ve since relocated to the Hudson Valley, where we manage homes across the Hudson Valley and the Berkshires, and we’re continuing to grow thoughtfully.

We also couldn’t have done any of this without Hospitable. We were honestly hesitant to move to a PMS at first, but Hospitable made the transition incredibly smooth — and the platform keeps improving faster than we can keep up (in the best way).

At the core, we’re owner-operators who built real systems from the ground up. That hands-on foundation is what allows us to step in as co-hosts and truly support homeowners who want better performance without the day-to-day burden.

Danielle

www.slowcations.com