Business Systems for a Short-Term Rental with Kassie Layne

I’m excited to dive into the topic of systems for short-term rental owners, something close to my heart as both a marketing strategist and a fellow short-term rental host.

I had the pleasure of talking about this with one of my favorite humans and behind-the-scenes business powerhouse: Kassie O’Driscoll.

Kassie is not only my best friend, but she’s also my go-to guru for all things business systems. As an Online Business Manager, she helps entrepreneurs whip their backend operations into shape so they can actually spend more time doing what they love. I’ve leaned on her expertise many times, whether for my branding agency or my event venue in Kentucky.

Together, we’ve both had hands-on experience managing short-term rentals. I got to turn the tables and pick her brain about how to build better systems in this unique space.

Why Systems Matter for Short-Term Rentals

When I asked Kassie how systems can help short-term rental (STR) owners save time and boost profits, she immediately brought up the misconception of passive income. If you’re not automating your rental processes, there’s nothing passive about it. From guest communications to property maintenance, managing a short-term rental can quickly become a full-time job.

Kassie emphasized that systems allow for quality control, something that helps owners not only save time but also create a consistent guest experience that earns those all-important five-star reviews.

Proximity Changes Everything: Local vs. Remote Owners

Something I’ve experienced personally, and Kassie confirmed, is that how close you live to your rental has a major impact on your systems and your mindset. If the property is right on your land or close by, you’re more likely to think, “I’ll just swing by to change the linens or fix this small issue.”

But that approach doesn’t scale, and it isn’t realistic for those of us who manage properties that are a car or even a plane ride away. Kassie’s seen it too: remote owners are far more willing to invest in automation tools, staff, and streamlined systems, simply because they have to.

The Cleaning Conundrum

I had to laugh when Kassie and I talked about cleaning. She nailed it. I can barely keep my own house clean, let alone a property I’m not in every day. It’s one of the biggest pain points in short-term rental management and an area that demands clear systems, reliable vendors, and realistic expectations.

Key Inefficiencies (and How to Solve Them)

Kassie broke down the most common inefficiencies into two categories:

For remote owners: The challenge is communication. If you’re hands-off, you must be proactive in making sure your cleaners, contractors, and platforms are all in sync. Otherwise, small issues can snowball quickly.

For on-site owners: The biggest issue is expectation setting. When it’s your home, it’s easy to assume everything is intuitive, but guests don’t know where the spoons are or how to work the TV. That kind of disconnect can result in frustrated messages and bad reviews.

My Real-Life Reminder: Personal Comfort vs. Guest Experience

One example that hit home for me literally involved one of the properties I manage, which is actually my mother-in-law’s house. They rent out the top two floors while living in the basement. As I was preparing a room upstairs for guests, I realized how tricky it is to shift from this feels like home to this feels like a hotel.

Small things like labeling remotes or making sure all personal items are stored away can make a world of difference. I even spotted how my mother-in-law had made subtle but smart changes over time to create more of a guest-first experience and it showed.

Anticipating Guest Needs

Kassie had such a good point here: when you live in the space, it’s hard to imagine what a first-time guest might struggle with. That’s why little details matter like labeling remotes, explaining where extra linens are stored, or providing instructions on how to use the coffee maker.

She shared one of her own core business philosophies that I absolutely love:

“If you’re asked the same question three times, build a system to address it.”

For short-term rentals, that often means creating a solid FAQ section, or even better, a guestbook. While digital guestbooks can be convenient, Kassie strongly recommends having a printed binder on-site. The first three guests will often raise the most important questions, and those should go straight into your system documentation.

Vetting Your Space with Fresh Eyes

One of the best pieces of advice we discussed is to have someone who isn’t close to the property stay in your rental before you go live. They’ll help uncover those small gaps in communication or comfort that you might miss.

For example, at our Kentucky rental, we kept getting questions from older guests on the Bourbon Trail about whether the bedroom was on the main floor. That feedback led us to update our listing and highlight that key detail.

Kassie had a similar experience managing a property for her parents. Guests had to walk down a long sidewalk to reach the Airbnb, and there was only a downstairs bathroom, two facts that needed to be clearly stated in the listing and in guest communication.

Automating Guest Communication from Day One

When I asked Kassie what communications should be automated right out of the gate, she didn’t hesitate:

• How to get to the property (especially if GPS is unreliable)
• Check-in instructions (door codes, lockbox locations, keypads)
• What to expect in terms of amenities (hot water, extra linens, pack-and-plays, etc.)
• Common area access (pools, fire pits, shared spaces)

And above all, she emphasized the importance of oversharing. Your guests are likely used to hotels, so anticipate their assumptions and address them proactively. Things like turn-by-turn directions from the highway or details about child accommodations can go a long way in making the experience seamless.

Personal Touch Without the Manual Labor

Automating communication doesn’t mean it should feel robotic. One standout strategy discussed is the personalized post-check-in message sent 12 to 24 hours after a guest’s arrival. This proactive check-in, written in a casual, friendly tone makes guests feel cared for without requiring the host to be online 24/7. It opens the door for guests to mention small issues they might otherwise ignore, leading to higher satisfaction and better reviews.

Interestingly, informal, text-style messages tend to get more honest responses than overly polished, formal notes. The hosts agree that casual messages foster a sense of connection and attentiveness. One even compares formal messages to automated “rate this experience” prompts that are easy to ignore. By making the message feel like a genuine text from a thoughtful host, guests are more likely to share real feedback.

Proactive Service Leads to Better Ratings

This small but powerful gesture of checking in during a guest’s stay often helps salvage a potentially average review. If guests are never given a chance to voice minor issues before checkout, they may deduct a star in their review, not out of spite, but because “it could have been better.” Taking initiative allows the host to resolve issues in real time, turning a 4-star review into a 5-star experience.

I also want to note a spike in private feedback on Airbnb after implementing the mid-stay check-in message. When guests feel like they’re talking to a real person who actually cares, they’re more inclined to provide constructive feedback directly instead of airing grievances publicly.

Checkout Instructions Should Be Clear—But Not a Burden

If guests are only staying for a few nights, communication after the initial check-in typically wraps up with a checkout message. This is sent the morning of their departure or late the night before, reiterating instructions already found in the guestbook. However, the tone and substance of these instructions are where many hosts get it wrong.

Kassie critiqued the all-too-common practice of charging high cleaning fees and expecting guests to do chores like laundry and dishes. Her stance? Treat your Airbnb like a hotel. Guests shouldn’t feel like they’re being punished with a long to-do list on their way out the door, especially after paying hundreds in cleaning fees. She understands that some requests (like taking out trash to avoid pests) may be necessary depending on the location or turnaround time between guests, but overall, fewer tasks mean happier guests.

Airbnb Communication: Why It Must Stay In-App

A critical point raised in the discussion is the requirement by Airbnb to keep all communication within the app. This protects both hosts and guests in case of disputes about damage, refunds, or other issues. While some guests, especially those from older generations, prefer to talk on the phone, it’s important for hosts to maintain a written record. A good workaround shared by the hosts is to follow up any voice call with a message in the Airbnb app, summarizing the conversation. This simple habit ensures all agreements are documented and easily accessible if Airbnb needs to get involved.

Add Local Flavor: Enhancing the Guest Experience

Beyond the basics, one thoughtful way to surprise and delight guests is by offering local perks. Kassie goes the extra mile by partnering with nearby restaurants to provide coupon codes or “mention our name” deals like free appetizers. She also includes information on delivery services and grocery options to make planning meals easier for guests. These personal touches aren’t just convenient, they make guests feel welcomed and valued.

Managing Multiple Booking Platforms

When it comes to hosting on multiple booking platforms such as Airbnb, VRBO, or a direct booking website, the process can quickly become overwhelming. Fortunately, there are tools available to centralize and streamline operations. A few recommended platforms include:

• Host Tools: A user-friendly and affordable option ideal for hosts with fewer properties. It offers automation features and calendar synchronization across multiple platforms.
• Hostaway: Better suited for property managers or hosts with five or more listings. It’s robust but comes with a higher price point.
• Lodgify: Another all-in-one solution, though its cost may not align with every host’s budget or needs.

For new hosts, Airbnb’s built-in automation tools have become increasingly capable. If you’re just getting started and hosting only on Airbnb, you can effectively use their internal systems to manage most workflows without needing additional software.

Dynamic Pricing and Manual Adjustments

While many platforms offer smart pricing or dynamic pricing features, not all hosts prefer to use them. The reason? The price you charge should reflect your business’s actual operating costs regardless of the season. Hosts should factor in their unique expenses, such as snow removal in the winter, and make manual adjustments accordingly.

While some pricing aspects, such as higher weekend rates or premium pricing for special events like the Kentucky Derby, can be set in advance, other nuances—, like wedding schedules or special circumstances, require manual oversight. In such cases, it’s essential to have a system in place to regularly review and update your calendar.

Syncing Calendars and Avoiding Conflicts

For hosts who manage properties connected to other operations, such as a wedding venue, there can be unique scheduling conflicts. For example, if an Airbnb is on the same property as a wedding venue, and the owner prefers not to rent the home out when there are weddings, even if the Airbnb isn’t being used by wedding guests, this adds a layer of complexity.

While tools like Host Tools can sync calendars across all booking platforms to prevent double bookings, there currently isn’t a known solution that syncs non-short-term rental systems (like wedding booking platforms) with short-term rental availability. These will remain manual touchpoints for hosts to manage.

Why Host Tools Stands Out

One of the standout features of Host Tools is its ability to automate communication not just with guests, but also with cleaning crews and other service providers. For example, the system can automatically send a text message to your cleaning team as soon as a new booking is confirmed. This is especially useful for hosts who manage properties from afar or have limited time to coordinate logistics manually.

Host Tools also offers messaging templates, calendar blocking, and integration across multiple platforms, making it a powerful all-in-one solution for short-term rental owners ready to take their operations to the next level.

Setting up a systemized, guest-focused short-term rental business isn’t just about automation. It’s about creating thoughtful experiences and efficient workflows that allow you to scale, save time, and delight your guests. Whether you’re managing one property or several, choosing the right tools and knowing when to automate versus when to manually intervene will make all the difference.