WiscoREIA Hayward: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story

STR Guest Experience Masterclass:

Turn Every Stay into a 5-Star Story

Click here to register!

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’s Hayward Meeting Always Meets on the 3rd Wednesday Month from

5:30 pm - 8:00 pm!

Hosts: Amanda Wilson and Marcus Eytcheson

Amanda Wilson is an alumna of the UW–Madison School of Business and the James A. Graaskamp Real Estate Program. She is an active member of the Wisconsin Real Estate Alumni Association (WREAA), WiscoREIA, and the founder of the Hayward Lakes REIA.

Since 2012, Amanda has owned and operated Deerfoot Lodge & Resort, a four-season family fishing resort on the Chippewa Flowage, Wisconsin's largest wilderness lake in Hayward, Wisconsin - an entrepreneurial endeavor that continues a cherished family vacation tradition and also launched her real estate investing journey. Over the years, she has expanded her portfolio to include storage, commercial, and residential rental properties, all driven by a mission to make the Hayward Lakes area an even better place to live, work, and play for generations to come.

When she’s not chasing real estate deals, you’ll likely find Amanda chasing muskies in her Lund Pro-V, either on the Chippewa Flowage or waters across the country.

Marcus has been involved in the construction industry for most of his life. Spending years working on different crews, doing sales for various contractors, and finally going to work with his team at Local Roofing. Marcus is now involved in the training, support, and management of the team here at Local Roofing.

Outside of roofing Marcus has a passion for investing in rural community businesses and real estate opportunities. Marcus is married to his wife Alisa Eytcheson with three young children Edwin, Esme, and Elon.

Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!

**Meeting Location**

Los Portales Mexican Restaurant

15546 Co Rd B

Hayward, WI 54843

Please enjoy food, drinks, and TIP YOUR SERVERS!

5:30 pm - 6:00 pm - Doors open early for Networking

6:00 pm - 8:00 pm - Speaker Presentation

The meeting ends at 8:00 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!

***Make sure to pre-register***

Click here to register!