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Short Term Rentals:How to Find It, Buy It and Get It Booked
Thinking about getting into short term rentals but not sure where to start?
Maybe you’ve looked at Airbnb or vacation rentals and wondered how people actually find the right property, figure out if the numbers work and then manage the property once they own it.
Ashley Lang is going to break it all down from beginning to end.
This presentation is built for someone who wants to understand the short term rental business and how to actually get started.
Ashley will cover:
✔️ How to identify markets that make sense for short term rentals
✔️ How to run the numbers before you buy
✔️ What realistic startup costs look like
✔️ Self management vs hiring a property manager
✔️ How to advertise through Airbnb and other OTAs, SEO and direct bookings
✔️ How to build a good local cleaning and maintenance team
✔️ What goes into operating a profitable short term rental
✔️ How to think about your long term hold and eventual exit strategy
If you’ve been thinking about short term rentals and want to understand what it really takes to get started, this meeting is for you.
Come spend an hour with Ashley and walk away with a much better understanding of how to find the right property, buy it, get it ready and start getting it booked.
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 40+ 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 three 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***
Your Hosts: Chris Hake | Ken Collins
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Event venue
18155 W Bluemound Rd, Brookfield, WI 53045-2935, United States
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