WiscoREIA upcoming events

WiscoREIA Sheboygan Falls: Rehabbing for Profit: Flip or Hold? (15 Jul 2026)

Wed, 15 Jul 2026 22:30:00 GMT

Rehabbing for Profit: Flip or Hold?

Every rehab project starts with a big question: Should you flip it for aquick profit, or hold it for long-term cash flow and wealth building?

Join us for a dynamic panel discussion featuring experienced real estate investors who have successfully used both strategies in today's market. Our panelists will share real-world experiences, lessons learned, successes, mistakes, and the factors they consider when deciding whether a property is best suited for a flip or a buy-and-hold investment.

During this interactive discussion, you'll learn:

✅ How to evaluate a rehab project and determine the best exit strategy
✅ The numbers and metrics investors use to make profitable decisions
✅ Current market conditions that influence flipping versus holding
✅ Common mistakes that can eat away at your profits
✅ Financing considerations for both strategies
✅ Real examples of deals that were flipped—and others that became long-term rentals
✅ How experienced investors balance cash flow, equity growth, and risk

Whether you're brand new to rehabbing or already working on deals, this session will provide practical insights you can immediately apply to your own investing business.

Bring your questions, connect with local investors, and gain valuable perspective from those actively doing deals in today's market.

Don't miss this opportunity to learn how successful investors decide when to flip, when to hold, and how to maximize profits either way!

Panelists: Nick Havlik, Joel Pipkorn and Tim Daughterty!

Nick Havlick

Nick Havlik, a dedicated real estate investor with 17 years of hands-on experience in the industry.

Nick got his start with a house-hack duplex, where he learned the ins and outs of managing tenants and rental properties firsthand. Since then, he and his wife have built a strong portfolio of multifamily properties throughout the Sheboygan area. They also previously owned and operated a successful Airbnb, giving them experience across multiple real estate investing strategies.

Outside of real estate, Nick is a technology education teacher and, together with his wife, owns and operates a 10-acre vineyard near Port Washington.

Nick brings a practical, real-world perspective to investing, balancing a full-time career, entrepreneurship, and long-term real estate portfolio growth. We're excited to have him share his knowledge and experience with our community.

Joel Pipkorn

Joel Pipkorn is a Wisconsin real estate investor, licensed Realtor, and entrepreneur with a passion for revitalizing properties and creating quality housing. After purchasing his first rental property in 2007, Joel steadily expanded his real estate portfolio while building and operating several successful businesses. Today, he owns more than 60 rental units, manages fix-and-flip projects, assists buyers and sellers as a Realtor, and is currently developing a 20-unit townhome condominium project in Sheboygan.

In addition to real estate, Joel is the founder of the Milwaukee-based entertainment company and cover band Detour. Whether he's growing businesses, developing properties, or performing on stage, Joel brings the same entrepreneurial spirit to everything he does. Outside of work, he enjoys spending time outdoors with his two children and sharing the value of hard work, financial freedom, and pursuing your passions.

Tim Daughterty

I’m a Christ-follower, husband, father, and full-time real estate investor with a passion for transforming properties and helping people. I began investing in 2008, and more than a decade ago I left my W-2 job to pursue real estate full time—a decision I’ve never looked back on.

Over the last five years, my team and I have completed 50+ deals across flips, rentals, and wholesales. As a landlord, we currently own 17 doors and growing, continually expanding our portfolio while improving the neighborhoods we serve. As the owner of Doc The House Buyer, LLC, our mission is to support homeowners throughout South Central Wisconsin, especially Rock, Jefferson, and Dane counties, by providing honest solutions for distressed sellers who need a trustworthy, timely option.

A core belief of mine is that once a student, always a student. I’ve spent the last 13 years learning, growing, and sharpening my craft through faithfully attending local REIA meetings, and that education continues today. Just as importantly, I’ve grown through serving and coaching others, paying it forward one person at a time. Helping new investors complete their first deals is one of the greatest privileges of my career.

I’ve successfully raised millions of dollars in private capital to fund real estate transactions, and I’ve built my business on two pillars: creativity and relationships. Whether structuring deals, solving complex problems for sellers, or collaborating with partners, these values have guided every step of my investing journey.

I’m committed to serving the Rock County community by sharing my experience, my network, and my passion for helping people build wealth through real estate. My goal is simple: to make a positive impact and empower others to succeed, both in business and in life.

WiscoREIA Sheboygan Falls' Meeting Always Meets on the 3rd Wednesday of the Month from

5:30 pm to 8:15 pm!

Host: Kyle Kaufman

Kyle Kaufman is a law firm owner, attorney, real estate investor, and host of the Meaningful Ideas Trading Club. Kyle was born and raised in Wisconsin. He grew up wanting to help people. He has discovered his life’s purpose to help families in Wisconsin and to provide individuals with commercial space for their business, and residences for people to live.

In 2005 Kyle started practicing law. He handled almost all aspects of the law. Early in his career he took on landlord and tenant matters, and civil disputes involving real estate. He started to advise people starting their real estate portfolios, and drafted documents for investors to use in their businesses and with tenants and property managers.

In 2010 Kyle became a one-third owner of the law firm, now known as HKK Law Offices (www.hkklawoffices.com). Kyle’s practice shifted to family law sometime around 2018, as more and more people called seeking his assistance. Kyle became fascinated with the financial information he discovered while representing individuals in divorce matters and financial disputes between former significant others. He started to study more thoroughly on the issues of real estate, business, taxes, and more.

Today, Kyle’s law practice focuses entirely on family law, including divorce, maintenance, child support, paternity, property division, child custody, adoption, termination of parental rights, guardianship and more. In the legal world, he sees his contributions in this area to have the most transformational impact on the community. An associate at his law firm practices estate planning.

Kyle now owns one-half of the law firm business and leads a team of 15 people.

Real estate has always been an interest, and after advising clients for many years, Kyle and his wife, Sunny, decided to join in on the fun. In the year 2020, Kyle and Sunny purchased a building with 18 residential units and two commercial units. In 2021, with a partner, they purchased two commercial properties. In 2022, Kyle and Sunny bought a 44,000 square foot warehouse with 3 parking lots. They sold the warehouse in 2025 for a profit. In 2025, they converted their Chicago condo into a rental unit, and then acquired 3 duplexes. They are generating passive income from their investments and using the power of delegation to make it all work.

In 2021 Kyle created an online weekly meetup event called the Meaningful Ideas Trading Club. Kyle hosts the program and invites others to share and mastermind on ideas related to personal and business development.

Outside of business, Kyle and Sunny have 6 children, and they enjoy spending their time with their family.

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

Meeting Location:

Legend Larry's

1142 Plankview Green Blvd

Sheboygan Falls, WI 53085

Please enjoy food, drinks, and TIP YOUR SERVERS!

Our Agenda

5:30 PM – Registration Check-In & Networking

• Informal networking with fellow investors

6:00 PM – Meeting Kickoff

• Welcome by Host and/or Co-Host

• WiscoREIA PowerPoint / announcements and updates

• Sponsor Introductions

• Haves & Wants – Share deals, services, and resources

6:30 PM – Deal Case Study

• Breakdown of a real deal with teachable moments (good, bad, ugly)

7:00 PM – Networking Breakouts

• Guest Orientation with Host

• Member & Sponsor general breakout for continued connection

7:15 PM – Main Presentation

• Host introduces Guest Speaker

8:15 PM – Closing Remarks

• Final thoughts and upcoming events

• Invitation to the "Meeting After the Meeting" for more networking

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!

WiscoREIA Sheboygan Falls: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story (19 Aug 2026)

Wed, 19 Aug 2026 22:30:00 GMT

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.