What I learned from an operator managing 200k+ booked nights

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What I learned from an operator managing 200k+ booked nights

Member since 2026 · 24 posts · 7 votes

Spoke with an operator managing a large STR portfolio (~200k+ booked nights).

They were able to automate ~70–80% of guest messaging.

But the biggest challenge wasn’t the AI.

It was building and maintaining the knowledge base behind it.

Made me realize:

AI works, but only if the operational data is structured properly.

Has anyone here tried automating guest messaging yet?

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John UnderwoodPro Member

Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes

6mo

I have such a great listing with pictures and description that I rarely get anything I need to respond to.

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John UnderwoodPro Member
Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
6mo
I have such a great listing with pictures and description that I rarely get anything I need to respond to.
3 Reply
- Izuchukwu Onukwube
  OP
  Member since 2026 · 24 posts · 7 votes
  6mo
  Quote from @John Underwood:
  
  I have such a great listing with pictures and description that I rarely get anything I need to respond to.
  That’s a great spot to be in, strong listings definitely reduce a lot of the basic questions.
  From what I’ve seen, the volume usually starts picking up more as you add properties or have overlapping stays across listings.
  
  Are you managing just the one property right now or a few?
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- John UnderwoodPro Member
  Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
  6mo
  Quote from @Izuchukwu Onukwube:
  
  Quote from @John Underwood:
  
  I have such a great listing with pictures and description that I rarely get anything I need to respond to.
  That’s a great spot to be in, strong listings definitely reduce a lot of the basic questions.
  From what I’ve seen, the volume usually starts picking up more as you add properties or have overlapping stays across listings.
  
  Are you managing just the one property right now or a few?
  
  We have 2. One I fully manage.
  0 Reply
Mike GrudzienPro Member
Lender · Eugene, OR · Member since 2019 · 2k+ posts · 1k+ votes
6mo
My 2 cents: I like inserting the human touch when I can.
1 Reply
Dave StokleyBusiness Member
Property Manager · Cleveland, OH · Member since 2015 · 705 posts · 799 votes
6mo
Yeah I mean that's how they work. It's not really AI, it's automation. It only knows what you tell it. Just like with VAs, the quality of what you get is directly related to the quality of what you put in.
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- Izuchukwu Onukwube
  OP
  Member since 2026 · 24 posts · 7 votes
  6mo
  Quote from @Dave Stokley:
  
  Yeah I mean that's how they work. It's not really AI, it's automation. It only knows what you tell it. Just like with VAs, the quality of what you get is directly related to the quality of what you put in.
  I actually agree with you.
  Most of what people call “AI” right now is just structured automation with better interfaces.
  
  The difference I’ve seen though is how well it handles variation. Traditional automations break the moment a guest phrases something slightly differently, whereas newer systems can still interpret intent and respond correctly *if* the underlying info is solid.
  
  But your point stands, garbage in, garbage out still applies. The real work is building good systems behind it, not just plugging in a tool.
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- Dave StokleyBusiness Member
  Property Manager · Cleveland, OH · Member since 2015 · 705 posts · 799 votes
  6mo
  Quote from @Izuchukwu Onukwube:
  
  Quote from @Dave Stokley:
  
  Yeah I mean that's how they work. It's not really AI, it's automation. It only knows what you tell it. Just like with VAs, the quality of what you get is directly related to the quality of what you put in.
  I actually agree with you.
  Most of what people call “AI” right now is just structured automation with better interfaces.
  
  The difference I’ve seen though is how well it handles variation. Traditional automations break the moment a guest phrases something slightly differently, whereas newer systems can still interpret intent and respond correctly *if* the underlying info is solid.
  
  But your point stands, garbage in, garbage out still applies. The real work is building good systems behind it, not just plugging in a tool.
  
  Yes that's true too, the "AI" part is interpreting what the guest actually needs. But yeah most things that people are calling "AI" right now are really just automation.
  0 Reply
Andrew SteffensBusiness Member
Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
6mo
I do about 15-20k booked nights per year, in my 10th year. AI is still new and I have yet to find a useful place for it other than assistant with building lists. Automations have been around since I started using PMS in maybe 2019 and I have 4 full time reservationists that get me 24/7 coverage. I think if I went over 100 listings I would need to add more than 1 reservationist on duty during peak hours, and I think that would be where I could leverage AI. However as of now, the cost does not make sense for me at my size to implement the AI as the automations and having an on duty staff member.
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- Izuchukwu Onukwube
  OP
  Member since 2026 · 24 posts · 7 votes
  6mo
  Quote from @Andrew Steffens:
  
  I do about 15-20k booked nights per year, in my 10th year. AI is still new and I have yet to find a useful place for it other than assistant with building lists. Automations have been around since I started using PMS in maybe 2019 and I have 4 full time reservationists that get me 24/7 coverage. I think if I went over 100 listings I would need to add more than 1 reservationist on duty during peak hours, and I think that would be where I could leverage AI. However as of now, the cost does not make sense for me at my size to implement the AI as the automations and having an on duty staff member.
  That makes a lot of sense, especially with a team already in place and solid coverage.
  At that level, it’s less about replacing staff and more about how much volume each person can handle efficiently.
  
  Out of curiosity, roughly how many guest messages does each reservationist handle per day?
  
  From what I’ve seen, the leverage point isn’t removing the team, but increasing how much each person can handle without adding more headcount as you grow.
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