STR Guest Experience Masterclass:
Turn Every Stay into a 5-Star Story
Click here to register!
Want to stand out in a saturated short-term rental market?
It’s not just about the property, it’s about the experience.
Join seasoned STR investor Ashley Lang (29 units and counting) for a no-fluff, real-talk presentation on delivering 5-star guest experiences that actually grow your business.
We’re talking:
✔️ How to create wow-factor moments without blowing your budget
✔️ Messaging strategies that prevent problems before they start
✔️ Handling guest drama like a pro (yes, even those guests)
✔️ Systems that make 5-star reviews the norm
✔️ The secret to turning one-time guests into loyal repeat bookers
✔️ How scale your STR portfolio
Whether you’re managing your first unit or scaling a portfolio, this session will give you tangible tools to elevate your guest experience, and your bottom line.
Speaker: Ashley Lang
Ashley Lang is a powerhouse real estate investor, short-term rental expert, and the founder of Clear Trail Properties. Since entering the short-term rental space in 2018, Ashley has built and scaled a high-performing STR portfolio rooted in one core belief: great design and great systems create great returns.
She currently owns and operates 25+ short-term rental units across Arizona, Central Wisconsin, Northern Wisconsin, and Michigan’s Upper Peninsula, while also scaling a rapidly growing co-hosting company managing an additional 20+ units across the same markets. In addition, Ashley oversees 25+ long-term rentals and flips single-family homes alongside her partner, Buck.
Ashley is known for her obsession with intentional STR design—from floor plans and furniture layouts to guest flow, durability, and the smallest finishing details. She believes design is not decoration; it’s a strategic tool that directly impacts occupancy, ADR, guest experience, and long-term asset performance. Her approach blends creativity with operational efficiency, ensuring properties are not only beautiful, but profitable and scalable.
Beyond building her own real estate empire, Ashley is passionate about teaching and coaching other investors to shorten their learning curve, avoid costly mistakes, and create freedom through real estate-backed businesses. Her work empowers others to confidently turn a vision into a high-performing short-term rental operation.
When she’s not running her companies, Ashley enjoys mountain biking, hiking, camping, and traveling with her boyfriend Buck, their son Korbin, and their four beloved bulldogs.
WiscoREIA Milwaukee Meeting Always Meets on the 2nd Tuesday of the Month from 6:00 PM - 8:30 PM!
Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!
Meeting Location:
DoubleTree Brookfield
18155 W Bluemound Rd
Brookfield, WI 53045
Please enjoy food, drinks, and TIP YOUR SERVERS!
Our Agenda
5:45 - 6:00 pm Check-in
6:00 - 6:45 pm Mini Vendor Tradeshow + Networking
6:45 - 7:00 pm Haves & Wants
7:00 - 8:30 pm Featured Presentation
The meeting ends at 8:15 PM, but we’ll continue with an informal after-meeting for anyone who’d like to stay.
You can stay after the meeting as well to network! Remember to bring your deals!
Our doors are open to EVERYONE!
***Make sure to pre-register***
Click here to pre-register!
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