At what point does guest messaging become overwhelming?

Question

Most people get into short-term rentals thinking it's passive income.

Then guest messaging hits.

Once you get past 15–20 properties, you're dealing with:

– constant check-in questions

– WiFi messages

– late-night requests

– repetitive guest questions

At what point did guest communication start becoming a real time drain for you?

Andrew Steffens · Answer

Most people do not have more than a handful of properties here.

Dave Stokley · Answer

I think we had around 15 when we hired our first full-time guest experience person.

Collin Hays · Answer

I hired once I passed 5 properties, but messaging was just a tiny part of that.  There are a lot of moving parts managing properties, with messaging being by far the easiest.

Jules Aton · Answer

I keep considering but this is my biggest hesitation to self manage. Being on call 24/7 isn't practical and actually sounds awful.

Izuchukwu Onukwube · Answer

Yeah, that’s probably the biggest reason most people hesitate to self-manage.

Koba Molenaar · Answer

My experience has taught me that guest communication is one major pain points, irrespective of how many properties you have. That's why I advise hosts to create templates. It's not just about saving time as you grow your STR business, but also helps you to keep calm when there's an annoying late-night request. @Izuchukwu Onukwube, what's your preference: hiring someone, using a system or both?

Pierre Guirguis · Answer

Most guest messaging is repetitive and predictable. Check-in instructions, WiFi, parking, house rules. That’s all stuff that can be handled through automation if the workflows are set up properly.

Where I think AI workflows start to make more sense is consistency and scalability. You’re not relying on someone to be available or respond the same way every time, and it doesn’t break once volume increases.

Interested in others' thoughts on this, do you still feel a human touch is necessary?

Koba Molenaar · Answer

@Izuchukwu Onukwube I see that you've founded Hostrexa, so you have firsthand experience into just how challenging guest communication can become. I like how you broke down the different stages. I absolutely agree with you — you need software help (at some stage), human oversight, and a system for how and when to use which resource (not just software, but cleaners, handymen, etc. too).

Full disclosure, I'm part of the iGMS team. So, from my experience working with hosts, I do believe templates stay relevant because as iGMS can automate message templates the effort doesn't necessarily grow as the volume increases.

That said, I think that many hosts need to use automation even when they have only between 1 and 10 properties already. It might not be for messaging, but to sync their calendars. And, as most vacation rental software solutions like Lodgify, Hospitable, Guesty, and iGMS have channel management and communication features, they might as well start automating guest communication when they only have a few properties.

Andrew Steffens · Answer

Never I just hired people after 10 properties and scaled.

At what point does guest messaging become overwhelming?

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