Isn't That Rich Podcast

If you have scrolled Airbnb lately, you have probably noticed it feels crowded out there. Cabins, cottages, guest suites, tiny homes, domes, even boats. Yet in southern Illinois there is a name that keeps coming up when you talk about five-star stays and smooth operations. Southern Illinois Vacation Rentals, led by owner and operator Allison Hasler. She just returned from the 2025 Vacation Rental Management Association conference and sat down with us to share what is really working in our market, where hosts are stumbling, and how she scaled from a couple of cabins to nearly fifty doors without losing her mind or her standards.

Below is everything we learned, packed into one friendly, no-fluff guide you can refer back to when you are shopping for a property, tuning up your listing, or deciding whether to hire a manager.

From 50ft Yacht Stays to Cabins in the Woods

Allison and her husband didn’t start in cabins — their first adventure in hospitality was floating. After selling a barge company on Lake of Egypt, they bought a 50-foot motor yacht on Kentucky Lake. Because he already had his captain’s license, they launched a pleasure-boat charter business, hosting birthday parties, bachelorette weekends, and family fun with Allison as first mate.

It was unique. It was experiential. And they loved it.

But when her husband was later diagnosed with rheumatoid arthritis, chartering became physically difficult. So they tried something new:
They tucked the yacht into a transient slip and listed it on Airbnb.

And that’s when everything changed.

The bookings poured in. Travelers were willing to pay a premium for an unforgettable experience, sleeping on a yacht included. That single shift lit the spark that would eventually become Southern Illinois Vacation Rentals.

That success pushed them closer to home, where they built small cabins on the back five acres of their property. Two turned into three, then into a small cluster. With each addition Allison built systems on the back end, from booking tools to cleaning checklists, until she realized the playbook would work for other owners too. One friend asked for help. Word spread. By 2021 she had a full-fledged management company, not a side gig. Today Southern Illinois Vacation Rentals manages almost 50 properties across the region and Allison still jumps in where needed, from guest communications to backup cleaning when a Saturday flip needs an extra set of hands.

The Hardest Part of Scaling

We asked what almost broke her. The answer was simple. Growing without enough process or people. In 2021 her portfolio doubled. The systems that worked for five properties did not work for ten. The systems that worked for fifteen did not work for twenty. Every bump of about five doors forced a change. New tech stack, a new contractor, a different workflow. The relief valve was hiring and delegating, even if someone else could only do a task at eighty percent of her own perfectionist standard. The business got better when she let go.

Today her team is a network of independent contractors. Cleaners, inspectors, bookkeeping, legal, maintenance. The headcount flexes with the seasons, which makes sense in a region where fall foliage and wine-trail weekends drive peaks through October.

What a Property Manager Does, and What You Still Own

A recurring theme with Allison is clarity. Before she takes on a client, she sends a slide deck that spells out exactly what her company handles and what remains with the owner. It saves everyone headaches later.

• She manages the guest experience, pricing, occupancy, quality control, and day-to-day issues that keep the stay five-star.

• You still own the responsibilities any homeowner would own. Land care, landscaping, trash service decisions, and the inevitable wear and tear that is not accidental or intentional damage. She will coordinate maintenance and can provide a maintenance team, but she is not a landscaper and she is not your social media manager.

This boundary is key. When managers try to be everything, the guest experience suffers and revenue follows.

Post-COVID Reality: Supply Is Up, Demand Is Different

For about a year and a half after COVID, supply and demand rose in parallel. City travelers escaped to rural areas, rates were low, and owners piled in. Now the supply remains high, but demand has normalized to pre-COVID patterns. Travelers are still traveling, but they are booking later and they have more options. That means success belongs to hosts who know exactly who they serve and curate for that person.

Allison’s north star guest is easy to picture. A midlife couple with or without kids, happy to pay for a private, beautiful space, but practical about cooking some meals at “home.” If your listing is stuffed with eight mismatched beds because you want to sleep fifteen people, you will attract a very different type of guest and a lot more headaches. Know your avatar, design for them, and price for them.

The Three Ingredients That Win in Southern Illinois

You asked and Allison answered. In our market the most consistently booked properties share three traits.

1. Small
   Studios and one-bedrooms do remarkably well. Two bedrooms with a pullout are great. They book midweek and off-season because couples travel more often than extended families.

2. Unique
   A-frames, thoughtfully designed new builds like the Tulipwood cabins, and anything with character beat generic houses with “grandma’s estate sale furniture.”

3. Hot tub
   You can roll your eyes, but the data is the data. A private soak after a day of hiking the Shawnee or hopping wineries sells.

If inventory is tight and a couple can choose between your empty ten-sleeper on the lake without summer weather or a cozy one-bedroom with personality, they will choose the one-bedroom nine times out of ten, even if the nightly rate is similar. Guests do not want to feel like they are paying for space they will not use.

Mid-Term Stays Are a Big Opportunity

One takeaway from VRMA that matters in southern Illinois. The mid-term market is growing. Think one to three months for contract workers. Construction crews on the west side of Marion, engineers servicing local industry, medical professionals on rotation, SIU faculty or grad students between leases, even remote workers on long assignments. Long-term landlords do not want to furnish. Short-term hosts do not want to give up premium weekends. That leaves a gap. If you furnish smartly and price by the month, you can keep strong occupancy with less turnover and less wear and tear.

Direct Bookings vs. Online Travel Agencies

We all say “Airbnb” as shorthand, but Airbnb, Vrbo, and Booking.com are simply online travel agencies. They provide reach and trust, and guests often stick with what they know. Yet there is real money on the table for both sides when you also offer a direct booking option. Service and host fees across platforms commonly add 15 to 20 percent to a reservation. A simple direct-booking site routed through your property management system can save repeat guests hundreds of dollars and save you thousands over a year. Allison still lists across multiple channels, but she actively nurtures direct bookings for owners who want to keep more of what they earn.

Cleanliness and Expectation Setting: The Two Non-Negotiables

Every successful host obsesses over two things.

Cleanliness. Floors get vacuumed and mopped every single turnover, whether the stay was one night or a week. Linens are spotless. Surfaces are sanitized. Checklists are written, signed, and enforced. Independent contractors get clear standard operating procedures and a fair market rate.

Managing expectations. Tell the truth in the photos and the copy. If the lake house has five flights of stairs, say it in the first paragraph, in the house rules, and in a labeled photo of the staircase. If there is a sweet but messy neighbor, say that the yard next door is unkempt so guests are not startled at check-in. If your place sits in a food desert, offer grocery delivery or a detailed prep list so families arrive ready. Use signage for everything with user error. Label multi-switch panels. Add a small laminated card next to the Nest thermostat with a QR code to the official how-to video. Make the house easy for Grandpa, not just the tech-savvy daughter who booked the trip.

Events, Occupancy, and Saying No Nicely

We get the question every week. “Can we host a wedding, a reunion, or add 30 day guests if the house sleeps 10?” The answer is no for most residential short-term rentals. Parking, trash service, septic load, and insurance are real constraints. Saying no does not have to be cold. Allison keeps a kind canned message, then recommends nearby venues or even beautiful state park locations when budgets are tight. It protects the property and it protects your reviews.

Pricing Like a Pro

This one change can add thousands a year. Use a revenue management tool. When Allison switched from static weekday/weekend rates to dynamic pricing powered by market data, her revenue jumped 65 percent over a six-month comparison. Tools like PriceLabs, Beyond, or Wheelhouse adjust for demand patterns you might miss, from bass tournaments on Lake of Egypt to home football weekends. You still steer the strategy, but you are no longer guessing.

Pair that with a property management system that pushes updates everywhere at once and you cut manual errors. Update photos, block Thanksgiving check-ins so your cleaners have the holiday off, or tweak a minimum-night rule, and every channel reflects the change.

Allison also watches a metric called Market Penetration Index. A 1.0 MPI means you are performing right at the median of your comps. She aims for 1.1 to 2.0. If you are higher than 2.0, your price is probably too low. If you are lower than 1.0, something in the offering or pricing strategy needs attention.

Licenses and Taxes in Illinois

One quick but important legal note from Allison’s experience. In Illinois there is no formal distinction between long-term and short-term property management in the licensing language. If you are doing property management activities for someone else, protect yourself with the appropriate leasing agent license sponsored by a broker. “Co-host” is an Airbnb word. Courts care about the activities you perform, not the label you use.

For taxes, expect occupancy or lodging taxes at the state, county, and sometimes city level, which you should collect from the guest and remit on schedule. Your manager can handle filings for occupancy taxes as part of the service, but you will still be responsible for your other taxes as an owner. If you do not pass occupancy tax to the guest, you still owe it.

What To Look For in a Manager

If you are interviewing managers, here are the green lights we look for based on Allison’s approach. Clear scope of work before you sign. Transparent billing with receipts attached for even small purchases. A maintenance pathway with pricing spelled out. Monthly owner statements that actually teach you how the property is performing, not just balances. And listening. Your property may have quirks or owner preferences. The best managers meet you in the middle as long as the guest experience stays high.

What’s Next for Southern Illinois Vacation Rentals

SIVR will cross 50 properties by year-end. Behind the scenes Allison is reorganizing workflows so the company scales without adding friction. On the guest side, expect more local touchpoints. Locally roasted coffee in the welcome kit, partnerships with artists and makers, and expanded enhancement packages like romance setups and grocery delivery for far-flung locations such as Elizabethtown. Thoughtful little details that make a trip feel curated instead of generic.

Should You Get Into This Business Here

Short answer. Yes, if you go in with open eyes. Our area still has room for well-designed small places that deliver a memorable experience. You can buy a turnkey short-term rental at a premium and operate from day one, or you can play the safer lane first with a mid-term rental aimed at contract workers. Either way, treat it like a business, not a hobby. Keep excellent records. Build for the guest you want. And plan your operation so it can function without you if life throws a curveball.

Want Help or Just Want to Talk It Through

Allison starts every engagement with a discovery call, then a clear slide deck that spells out responsibilities and numbers. From there she and the owner work a shared checklist to launch. If you want to explore management, find her at Southern Illinois Vacation Rentals. Search the name or head to sivr.rentals to reach the management page and connect.

And if you are a host or a curious future investor, tell us which part you want us to unpack next. Direct bookings, mid-term setups, pricing tools, or the complete “guest experience” checklist. We are happy to bring Allison back and go deep on the topic that will help you most.