WiscoREIA upcoming events

WiscoREIA Hayward: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story (20 May 2026)

Wed, 20 May 2026 23:30:00 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 Hayward Meeting Always Meets on the 3rd Wednesday Month from

5:30 pm - 8:15 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 - 8:15 pm - Speaker 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 register!

WiscoREIA Hayward: Mastering Tax Planning! (17 Jun 2026)

Wed, 17 Jun 2026 23:30:00 GMT

Mastering Tax Planning:Protect Your Wealth and Your Deals!

Click here to register!

In 2024, we're seeing a surge in IRS liens and garnishments, making effective tax planning more crucial than ever. The IRS is ramping up collections, and it's essential to navigate these waters with confidence.

Here’s what Amy will cover:

Tax Planning, Not Paying: Focus on strategic tax planning to minimize your liabilities.
Ensuring Proper Tax Structures: Ensure you have the right entities in place.
Choose the Right Tax Preparers and Bookkeepers: Collaborate with experienced professionals who understand the intricacies of tax regulations.
Common Deductions People Miss: Don’t leave money on the table!
Dealing with Increased Collections: If you find yourself facing collection actions, know your rights.
What to Do If You Get a Notice from the IRS: Don’t panic!
Handling IRS Liens and Garnishments: If an IRS lien or garnishment threatens your business deals, act quickly.

The key to thriving in today’s tax landscape is knowledge and preparedness. Equip yourself with the right resources, and don’t face the IRS alone.

Speaker: Amy Farrow

Amy Farrow is an Attorney and real estate investor with over twenty-five years of experience. She has represented business owners, banks, and real estate professionals in litigation and transactional matters. Amy has also closed hundreds of real estate transactions, residential and commercial. She has bought and flipped more properties than she can remember, the very first in 1999.

Amy is a graduate of the University of Wisconsin, both undergraduate and law school. She began her practice of law at a small firm servicing Columbia, Sauk and Dane County. After a few years of practice, Amy joined the Department of Justice. She served as a Special Agent with the Federal Bureau of Investigation in Oklahoma City, OK. After five years, Amy returned to Wisconsin and resumed the practice of law serving southeastern Wisconsin.

In her spare time, Amy loves to relax with her four children and two silly dogs. She and her husband travel often and love to visit National Parks. Amy also runs in obstacle and adventure races several times a year, such as the Tough Mudder and the Spartan races. She is a commercial pilot and is currently looking to buy a plane for new adventures. Amy also sits on the board of a nonprofit that focuses on raising money for breast cancer survivors and their families.

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

5:30 pm - 8:15 pm!

Hosts: Amanda Wilson and Marcus Eytcheson

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.

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 - 8:15 pm - Speaker 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 register!

WiscoREIA Hayward: Exploring AI Tools for Real Estate Investors (15 Jul 2026)

Wed, 15 Jul 2026 23:30:00 GMT

Exploring AI Tools for Real Estate Investors

Click here to register!

Artificial Intelligence is transforming the way we work—and real estate investors are already putting it to use. From deal analysis and research to marketing and property management, AI tools are quickly becoming must-have resources for anyone serious about scaling their business.

This month, we’re hosting an interactive discussion on the AI tools investors are using right now. This won’t be a sit-back-and-listen session—we’ll have someone live on the computer pulling up sites and tools as they’re mentioned, so you can see them in action.

✅ Discover tools that can save you time and boost efficiency
✅ Learn how fellow investors are applying AI in real-world scenarios
✅ Share your own go-to resources and success stories

Whether you’re already experimenting with AI or just starting to explore what’s out there, you’ll leave with actionable insights and practical tools to take your investing to the next level.

Speaker: Ken Collins

Ken's journey began in the field of social work and psychotherapy, where he dedicated a decade to helping others navigate their personal challenges. Seeking new horizons, he transitioned into the tech industry, joining Hewlett-Packard. Over the next 24 years, he evolved from a Computer Engineer to a Global Project Manager, culminating in his leadership of the Global Sales Lead program, which under his stewardship generated nearly $1 billion in sales each year.

In 2016, Ken pivoted to real estate investing, initially employing the BRRRR (Buy, Rehab, Rent, Refinance, Repeat) method. Upon retiring from corporate life, he focused on creative deal structuring, mastering techniques like Subject-To (Sub2), Lease/Options, and Land Trusts. His portfolio includes over 50 Real Estate transactions in the last 8 years, ranging from mobile homes, single family and multifamily properties, showcasing his versatility and expertise in the real estate market.

Ken credits much of his real estate knowledge and sharpened skills to his active participation in the many WiscoREIA Madison education programs. Through joining their Coaching Program, completing the Blueprint course, and engaging in numerous educational opportunities including hands-on property tours and weekend training events from a variety of speakers sponsored by the REIA, Ken has continuously expanded his expertise in real estate.

Ken is renowned for his proficiency in lead generation and deal negotiation, leveraging a multitude of creative strategies to craft win-win scenarios in real estate. He now steps into his role as a coach for aspiring real estate investors, eager to share his knowledge and experience. He is always on the lookout for personal growth opportunities, being an active member of groups like Lifeonaire and the Generations of Wealth Mastermind group, which further fuel his passion for continuous learning and development.

With a life that beautifully blends family, community, technology, and real estate, Ken Collins is not just a coach but a mentor who understands the art of building wealth through real estate while maintaining a life of balance and fulfillment.

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

5:30 pm - 8:15 pm!

Hosts: Amanda Wilson and Marcus Eytcheson

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.

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 - 8:15 pm - Speaker 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 register!