Trying to work out where the breakeven sits on guest communication.
If you're at 3+ doors: do you pay a VA, use a co-host, or still handle messages yourself? Roughly what does it cost you a month, or how many hours?
Curious whether people hand it off at 3 doors, 5, 10, or never.
Most of the questions can be answered with a template. "Can we check in earlier? Can we check out late? Can we drop off our luggage? Can I have someone come for dinner but not stay overnight?" Most questions are super common. Occasionally I have to deal with guests asking harder questions :)
I manage 4 properties all by myself and I don't use a VA, because it's interesting, some guests really prefer interacting with the host. I personally travel and use Airbnb a lot, and it's really annoying to chat with a VA or AI, because the hard questions always get escalated to the owner anyway.
But I do hope to use a co-host once my portfolio is bigger. At 10+ properties you need someone you trust who can run day to day operations while you scale to the next one. A VA won't do that.
Scaling is one thing, maintaining what you have is also important. Doesn't matter who you hire at the end of the day, whether it's a VA, AI agent, or co-hosts, you need to make sure they keep your foundation solid, so you can lay breaks on top.
I hit 10-15 units in 2017 or 2018 well before many of the tools on the market today were available and I did it all myself. From that point on I did hire VA's, who still work for me today. This all depends on what else you have going on if your life as well.
10-15 solo is more than anyone else said, that surprised me.
What do your VAs actually spend the time on now? Trying to work out how much of it repeats and how much really needs a person.
I have 4 VA's that provide around the clock coverage. At about 60 units they are busy at peak hours and usually less busy during the off peak times. The off peak times get admin assignments given to them as well to complete in a certain amount of time.
All a matter of the value of your time.
Most of the questions can be answered with a template. "Can we check in earlier? Can we check out late? Can we drop off our luggage? Can I have someone come for dinner but not stay overnight?" Most questions are super common. Occasionally I have to deal with guests asking harder questions :)
I manage 4 properties all by myself and I don't use a VA, because it's interesting, some guests really prefer interacting with the host. I personally travel and use Airbnb a lot, and it's really annoying to chat with a VA or AI, because the hard questions always get escalated to the owner anyway.
But I do hope to use a co-host once my portfolio is bigger. At 10+ properties you need someone you trust who can run day to day operations while you scale to the next one. A VA won't do that.
Scaling is one thing, maintaining what you have is also important. Doesn't matter who you hire at the end of the day, whether it's a VA, AI agent, or co-hosts, you need to make sure they keep your foundation solid, so you can lay breaks on top.
Thanks Angela, that's useful. The escalation thing is the part I keep hearing, and it annoys me as a guest too.
Quick one, if the host replies within a minute or two does it still bother you? Or is it being handed off at all that's the problem?
Thanks Angela, that's useful. The escalation thing is the part I keep hearing, and it annoys me as a guest too.
Quick one, if the host replies within a minute or two does it still bother you? Or is it being handed off at all that's the problem?
Actually, most of my guests really appreciate that I reply fast. If you use AI, you just have to give a correct prompt to your AI system, so it behaves just like a human.
@Martin Jahoda
I think it depends less on the number of doors and more on how much your time is worth. Some owners are happy managing 3–5 properties themselves with good automation, while others outsource guest messaging much earlier so they can focus on acquisitions and asset management. Having solid systems in place first usually makes outsourcing a lot smoother.
I'm at 4 doors now and still self-managing messages, but I automated the repetitive stuff about 18 months ago. Honestly, that's where the math changed for me.
Before automation, I was spending 3–4 hours a week on guest comms: check-in instructions, standard questions about parking, wifi, checkout time, review follow-ups. The VA route looked like $300–500/mo minimum, which felt steep when a lot of it was just templated responses.
I use a tool that handles templated messages (check-in sequence, common questions, review requests) and auto-flags anything that needs a personal touch. Cut my actual active time to maybe 30 mins a week. Cost is negligible compared to hiring someone.
For the breakeven: I'd say if you're at 3 doors and spending 5+ hours/week, a VA makes sense. But if your messages are 60% templatable (and they usually are), automation buys you breathing room without the monthly fee. A lot of hosts I know go full PM around 8–10 doors, but that's more about turnover coordination and maintenance than just messages.
What's your current weekly time on comms?
From a tax strategy standpoint, guest communication makes up a real portion of your material participation hours if you're using the STR loophole or REPS. Outsourcing it doesn't disqualify you, but it does shrink your claimable hours, so make sure you're still tracking cleaning coordination, pricing updates, and maintenance decisions to hit whichever IRS test threshold you're relying on.
The VA or co-host fee itself is a standard deductible expense against rental income, the real impact is how it affects your participation tracking.
Happy to connect!
Marin,
First, congrats on getting to three doors! That's a great milestone. Those first few properties are often the hardest because you're building the systems that will help you scale.
I think this has less to do with the number of doors and more to do with the quality of the experience you're providing while making the best use of your time.
AI is becoming the a great tool in managing rentals, and it can save a tremendous amount of time. The key is making sure it's trained well enough to answer questions accurately and in a way that reflects how you want to communicate. If it isn't, you can end up spending more time correcting mistakes or handling escalations than you save.
One thing we often said in the early days of building RentRedi was, "Do what doesn't scale." We intentionally held off automating some customer interactions because those conversations taught us what people were actually asking, where they were getting stuck, and what they needed. In hindsight, that helped us build a much better product.
I think the same principle applies here. Before completely handing communication over to AI or a VA, it's valuable to understand the common questions and pain points yourself. Once you do, templates and AI become much more effective because they're built on real-world experience.
For many landlords, the right answer is a hybrid approach: automate the repetitive questions, personally handle the situations that require judgment, and periodically review conversations to make sure the experience stays high quality. Ultimately, it's about balancing cost, your time, and the level of oversight you're comfortable providing
I hope that helps.
Hope to see you at BPCON in Orlando!
One door.
After manually doing the guest communication for a few weeks with our first STR, I decided to automate it.
Mike
