WiscoREIA Wausau: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story (16 Nov 2026)

Tue, 17 Nov 2026 00:00:00 GMT

STR Guest Experience Masterclass:

Turn Every Stay into a 5-Star Story

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’s Wausau Meeting Always Meets on the 3rd Monday of the Month from

6:00 pm - 8:30pm!

Hosts: Derek Dombeck & Cayla Farley

Derek has been a successful Investor since 2002. He’s been through the ups and downs of the markets and has the scars to prove it.

Derek has been involved in hundreds of transactions in his career. He’s done wholesaling, flipping, landlording, lending and countless other investment strategies throughout the years.

Derek loves negotiating with sellers. He loves to put together creative solutions for sellers that few other investors can put together.

Derek loves giving back to the real estate community. Derek is also a coach and mentor who has a passion for helping others be successful too.

Cayla and Brandon are a dynamic husband-and-wife real estate investing team based in Wisconsin. As parents of two and long-term investors, they’ve built their business around transforming outdated single-family and multifamily properties into strong, sustainable assets designed for long-term growth.

Beyond real estate, they also own and operate a successful fence installation company, giving them a hands-on, operations-driven perspective that sets them apart. When they’re not managing projects or growing their portfolio, Cayla and Brandon love spending time outdoors, staying active, and making memories with their kids—proof that it’s possible to build a thriving business while prioritizing family and lifestyle.

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

Meeting Location:

The Bar

10302 Market Street

Rothschild, WI 54474

Please enjoy food, drinks, and TIP YOUR SERVERS!

**Time**

6:00 pm - Doors Open & Check-in

6:30 pm - Meeting Starts

7:00 pm - 8:30 pm - Speaker Presentation

The meeting ends at 8:30 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!

WiscoREIA upcoming events

WiscoREIA Wausau: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story (16 Nov 2026)