At what door count did you stop answering guest messages yourself?

Question

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.

Angela Venger · Answer

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.

Andrew Steffens · Answer

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.

Andrew Steffens · Answer

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.

Collin Hays · Answer

All a matter of the value of your time.

Ruka Tsunoda · Answer

Jumping in on the Martin/Angela exchange about whether fast replies fix it or any handoff is the problem — I think Angela's point about giving the AI a correct prompt is actually the whole answer. Guests generally can't tell, and don't care, whether a human or a system replied if the response is fast and actually correct. What breaks is when the exception rules were never written down: a generic AI/VA setup handles the FAQ fine, but hits something like a broken lockbox or a neighbor complaint and has no instruction for what to do, so it punts to the owner, not because it's incapable, but because nobody defined the judgment call in advance.

So the door-count question is kind of a proxy for how much of your actual escalation logic you've ever written down. Some hosts do that early at 3 doors, some never do it at 30, and that's the bigger driver than unit count.

That specific translation, turning a host's actual judgment calls into rules something automated can follow instead of a generic AI concierge, is what I work on. Not pitching here, just adding a data point to the thread.

Mike Shemp · Answer

One door.After manually doing the guest communication for a few weeks with our first STR, I decided to automate it.Mike

Ed Barone · Answer

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 providingI hope that helps.  Hope to see you at BPCON in Orlando!

Angela Venger · Answer

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.

At what door count did you stop answering guest messages yourself?

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