Real estate investment news you can use!

May 2026

MESSAGE FROM THE BOARD

The Biggest Mistake New STR Investors Make in the First 90 Days

If I had to boil it down to one thing, it’s this:
Most new short-term rental investors underestimate the operational side of the business.

Not the purchase. Not the financing. Not even the design. The operations. When most of us get into short-term rentals, we come from a traditional real estate mindset. We’re used to thinking like landlords. Find a good deal, fix it up, get it rented, and collect checks. Simple. Short-term rentals look similar on the surface… but they are a completely different business underneath. You’re not just buying a property. You’re running a hospitality business. And in the first 90 days, that reality hits hard.

Mistake #1: Treating It Like a Rental Instead of a Business
This is the root of everything. A long-term rental is relatively passive once it’s stabilized. A short-term rental is interactive.
You have:

Frequent guest communication
Regular turnovers
Ongoing maintenance
Constant pricing adjustments

If you don’t build systems early, you end up reacting instead of running the business. And reacting is exhausting and will likely burn you out quickly.

Mistake #2: Underestimating the Importance of Cleaners
I’ll say this as clearly as I can: Your cleaner can make or break your STR. Not your kitchen remodel. Not your furniture. Not even your location (within reason). Your cleaner. They are the last person in the property before your guest arrives. They control the first impression, and in many ways, they control your reviews. In the first 90 days, a lot of investors simply hire the cheapest option, don’t set clear expectations, don’t create a checklist, assume “clean is clean”. But in short-term rentals, there’s a difference between: “Looks clean” and “Guest-ready”. Guest-ready means:

Everything is staged the same way every time
No missed details (hair, crumbs, fingerprints)
Supplies are restocked consistently
Issues are reported immediately

A great cleaner isn’t an expense, they’re a partner in your revenue.

Mistake #3: No Systems = Constant Stress
If you feel like you’re “on call” all the time, it’s usually not because the business is broken. It’s because there are no systems. In the first 90 days, you should be thinking about:

Messaging templates (so you’re not rewriting the same responses)
Turnover checklists
Supply restocking systems
Maintenance processes
Guest expectations (set clearly in your listing and messages)

Without these, every guest feels like a new situation. With systems, the business becomes predictable. And predictable is where freedom starts to show up.

Mistake #4: Pricing Based on Guesswork
This is a big one—and it directly impacts your bottom line. I’ve seen new investors either:

Price way too low to “get bookings”
Or price too high without understanding their market

Both cost you money. Before you even go live, you should spend time deeply researching comparable listings in your area.
Look at:

Bed and bath count
How many guests they comfortably accommodate
Amenities offered
Design quality
Reviews and ratings
Pricing across weekdays, weekends, and seasons

You want to understand:
“Where does my property fit in this market?”
If you’re in a more competitive or STR-heavy area, manual pricing can only take you so far. That’s where tools like PriceLabs can be incredibly helpful. They adjust your pricing dynamically based on demand, seasonality, and local trends, something that’s very hard to do consistently on your own. At the end of the day, pricing isn’t set-it-and-forget-it. It’s a lever you should be adjusting regularly.

Final Thought
Short-term rentals can be an incredible wealth-building tool. They’ve certainly been that for my family. But the investors who succeed long-term aren’t just the ones who buy the right properties. They’re the ones who learn how to run the business well. If you can get a handle on operations early, cleaners, systems, and pricing you don’t just reduce stress, you increase consistency. And in this business, consistency is what leads to:

Better reviews
Higher occupancy
Stronger revenue

The first 90 days matter more than most people realize. Treat them like the foundation… because that’s exactly what they are. Don’t forget we host a STR discussion meetup every 3rd Monday of the month at Portillo's in Batavia IL on Randall Road. We start @ 7pm. Join us for casual conversations about STRs.

Steven Bell
Chicago Area Real Estate Investors Association - Vice President

Upcoming Events

CAREIA

Board of Directors

CAREIA Monthly General Meeting

Monday, May 11, 2026 @ 7:00 p.m.
Networking starts at 6:45 p.m.
Hyatt of Lisle • 1400 Corporetum Drive, Lisle

Topic: Practical AI Use in Real Estate Investing

Key Note Speaker: Sam Gorgey

https://www.careia.org/event-6583612

Short Term Rental Sub Group Meeting

Monday, May 18, 2026 @ 7 p.m.

Portillo's Hot Dogs, 531 N. Randall Rd., Batavia, IL 60510

A FREE Member & Non-member Event

Anyone who has an interest in investing in short or mid-term rentals are invited to attend our monthly STR sub group meeting. Each month we will have an open forum to discuss all things short term rentals.

https://www.careia.org/event-6640156

Real Estate Networking Night

Monday, May 25, 2026 @ 6:30 p.m.

Portillo's Hot Dogs, 235 E. North Avenue, Glendale Heights, IL 60139

A FREE Member & Non-member Event

https://www.careia.org/event-6640158

Cash Flow Game Night (Members Only Event)

Wednesday, June 3, 2026 @ 7:00 p.m.
McDonald's off Highland Avenue
1 Yorktown Shopping Center, Lombard

https://www.careia.org/event-6640162

CAREIA Monthly General Meeting

Monday, June 8, 2026 @ 7:00 p.m.
Networking starts at 6:45 p.m.
Hyatt of Lisle • 1400 Corporetum Drive, Lisle

Topic: Infinite Banking & Real Estate Investing

Key Note Speaker: David Cheatham

https://www.careia.org/event-6583536

Short Term Rental Sub Group Meeting

Monday, June15, 2026 @ 7 p.m.

Portillo's Hot Dogs, 531 N. Randall Rd., Batavia, IL 60510

A FREE Member & Non-member Event

https://www.careia.org/event-6640165

Real Estate Networking Night

Monday, June 22, 2026 @ 6:30 p.m.

Portillo's Hot Dogs, 235 E. North Avenue, Glendale Heights, IL 60139

A FREE Member & Non-member Event

https://www.careia.org/event-6640167

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WORDS OF WISDOM

“You do not rise to the level of your goals. You fall to the level of your systems.”

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Library Book of the Month

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James Clear

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And much more.

Get it now!

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