Fellow STR operator looking to compare notes with a few hands-on hosts

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Fellow STR operator looking to compare notes with a few hands-on hosts

Adhirai M.
Investor · Seattle, WA · Member since 2021 · 15 posts · 8 votes

Hi all, I'm Adhi, and my partner and I self-manage our own short-term rentals.

The part that never really stops for us is the daily operational load: guest messages at all hours, chasing cleaners and vendors, turnovers, the little things that slip when you're busy or traveling. I'm trying to get sharper about how other hands-on hosts handle it, so a few honest questions:

– How do you keep guest messaging from eating your evenings? Templates, a VA, automation, something else?
– What's your system for coordinating cleaners and maintenance when you're traveling or off-grid?
– Where do things most often fall through the cracks for you?

Happy to share what's worked (and what's badly failed) on our end too, we've tried a lot. Even if you only manage one property, I'd love to hear how you run things.

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John UnderwoodPro Member
Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
2w

I almost never get messages from guests other than thank you for the treat you left us and the house is great!

I have a very detailed description in my listing and pictures of things that answer questions.

Make sure you describe the grill and the coffee pot/s. Those used to be my two most asked questions.

I might get a question about the lake or our dock, but this is also rare.

I have a hard copy of the house manual laying on the kitchen table so it is easy to flip through and get answers.

What type of questions are you seeing. Can you add a better description or pictures to cut down on the most common questions?

As far as cleaning schedule. We let our cleaners know when we have new bookings and she adds them to her calendar. Another way is to have a synced and shared google calendar with your scheduled stays.

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  • John UnderwoodPro Member
    Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
    2w

    I almost never get messages from guests other than thank you for the treat you left us and the house is great!

    I have a very detailed description in my listing and pictures of things that answer questions.

    Make sure you describe the grill and the coffee pot/s. Those used to be my two most asked questions.

    I might get a question about the lake or our dock, but this is also rare.

    I have a hard copy of the house manual laying on the kitchen table so it is easy to flip through and get answers.

    What type of questions are you seeing. Can you add a better description or pictures to cut down on the most common questions?

    As far as cleaning schedule. We let our cleaners know when we have new bookings and she adds them to her calendar. Another way is to have a synced and shared google calendar with your scheduled stays.

    3Reply
    • Adhirai M.
      OP
      Investor · Seattle, WA · Member since 2021 · 15 posts · 8 votes
      2w
      Quote from @John Underwood:

      I almost never get messages from guests other than thank you for the treat you left us and the house is great!

      I have a very detailed description in my listing and pictures of things that answer questions.

      Make sure you describe the grill and the coffee pot/s. Those used to be my two most asked questions.

      I might get a question about the lake or our dock, but this is also rare.

      I have a hard copy of the house manual laying on the kitchen table so it is easy to flip through and get answers.

      What type of questions are you seeing. Can you add a better description or pictures to cut down on the most common questions?

      As far as cleaning schedule. We let our cleaners know when we have new bookings and she adds them to her calendar. Another way is to have a synced and shared google calendar with your scheduled stays.

      @John Underwood - Good tip on the house manual. Even with one though, I still get guests who'd rather just text me a quick question than look it up.

      How's the cleaning and maintenance side gone for you? Guest messages I can mostly stay on top of, but a cleaner not showing up or a repair coming up while I'm out of town is what really gets me. Have you got that part figured out too?
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    • John UnderwoodPro Member
      Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
      2w

      Never had any trouble with cleaners. I have had different ones over the years, but they have always been there on cleaning day.

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  • Trent Reeve
    Atlanta · Member since 2022 · 706 posts · 634 votes
    2w

    I self manage 3 and manage 5 for clients while also having my full time W2 job. Happy to discuss how i handle everything.

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  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    2w

    How many units do you have. There are solutions to every "problem", VA for messages, software to assist in turnovers, etc. However, if you are managing less than 5-10, these are not really necessary and are an undue cost. At 5-10, Google Docs and Sheets and a few free apps and smart tech can solve pretty much any problem.

    [email protected]813-563-0877
    Vacation Rentals of Florida53 Reviews
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  • Carolyn Fuller
    Cambridge, MA · Member since 2015 · 649 posts · 732 votes
    2w

    I manage 2 STRs and try very hard to avoid listing them at the same time. This means, at any given moment, I only have 1 STR I'm managing.

    I mostly don't travel when I'm listing either of my STRs. I found that Murphy's Law prevailed if I attempted travel while active hosting. I even had paid someone to be my on-the-ground host while I was traveling but the extremely rare problems that erupted while I was away were beyond the capability of our paid host to handle. Hence, no travel while actively hosting. I rent my listings for 3+ months when I plan on traveling. This is easy to do since I live in a college town and prefer to travel during cooler weather, which is anytime other than the summer. Since I can easily rent 3+ months between Sep - May and since summer is the height of the STR season, this timing works well for me.

    I take advantage of Airbnb's listing specific auto-messages and templates. I have a home manual both within Airbnb with hard copy in the STR. I get very few questions and those I do get are easy to manage. When I do get questions that I think might be repeated in the future, I create a template for responding. Even when I can't avoid listing both of my STRs at the same time, the listing specific auto-messages and templates are a godsend. I've never gotten confused about which listing a guest is staying in.

    0Reply
  • Diana Khan
    Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 296 posts · 111 votes
    2w

    @Adhirai M., one thing I’ve learned from owning property and running businesses is that the biggest problem usually is not the number of messages. It is when every message feels like it needs your attention right away.

    I would separate things into a few simple groups. An access problem, safety issue, major repair, or upset guest may need a person quickly. A question about Wi-Fi, parking, check-out, or how something works should already have a clear answer somewhere.

    I’ve also learned to pay attention to anything that keeps happening. If guests ask the same question three or four times, that tells me the process needs to change. If the same cleaner or vendor issue keeps coming back, that is probably not a reminder problem anymore. It is a system or people problem.

    For me, the goal would not be to automate everything. I would want the routine things handled without me, so I still have time for the situations that actually need judgment.

    That is usually where I see the biggest difference between a system that helps you and one that just gives you more notifications.

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  • Mike Shemp
    Rental Property Investor · Stewartsville, NJ · Member since 2016 · 418 posts · 280 votes
    2w

    I manage 3 with a full-time job.

    • I use Hospitable for guest/cleaner communication, and where they fall-short on automation I do it myself with Zapier and Claude Co-work.

      After 10pm guests get an auto-message that I'll respond to them in the morning and to call me if true emergency (fire, flood, or blood).

    • They get a digital guidebook link that I built on Notion.io (free). I did this to replace the paid digital guide book services. There is also a hardcopy guidebook at the properties.

    The most common question I get is "how to get the cable/tv working" and I have an auto-message response for that with detailed instructions.

    Hope that helps.

    Mike

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  • Collin HaysBusiness Member
    Property Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
    2w

    We have a team effort.  There are three of us on the messaging system. Whoever has a free minute answers the message - morning, noon, or night.

    Part of running a short term rental hotel business.

    [email protected]806-672-7102
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  • Matthew Tregoning
    Real Estate Consultant · Melbourne, FL · Member since 2019 · 185 posts · 104 votes
    2w

    Pay the backup cleaner to do a real turn before you need them. A phone number in your contacts isn't much of a backup if they've never been inside. I'd want someone local who can handle a small repair without waiting for me too.

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  • Mehtap Baglan
    Real Estate Consultant · Ankara, Türkiye · Member since 2026 · 6 posts · 1 vote
    2w

    I think the biggest operational issue starts when information gets scattered across too many places. Cleaner communication might be in WhatsApp, turnover details in a spreadsheet, maintenance somewhere else, and inventory gets checked only when someone notices something is running low.

    What seems to work better is having one central operational view for each property — turnovers, cleaner follow-up, inventory/restocking and maintenance — even if WhatsApp or other tools are still used for the actual communication.

    It also helps to make every turnover a repeatable checklist rather than relying on messages or memory. That way, a missed restock or maintenance issue is easier to catch before the next guest arrives.

    For those managing several STRs, I'm curious: which becomes difficult to stay on top of first as you grow — cleaner follow-up, inventory/restocking, or maintenance?

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