We Bought Land (Part 2): Use ChatGPT in Your STR Competitive Analysis (Episode 361)

Airbnb Hosts Hanging Out in the Kitchen

Pro Tips for Planning, Competitive Analysis, Outsourcing

Welcome back to this dedicated series on the acquisition, set-up, and launch of our brand new Hocking Hills vacation rental project. In this episode, we update listeners on the actions we’ve taken since signing the deal, hard decisions we’ve already made, and what’s coming up next.

Golden nuggets include how Sarah has leveraged artificial intelligence to create temporary branding for the property, early thoughts on how we might utilize existing structures (or not), and which critically important tasks we’ve already elected to outsource – two jobs you’ll be very surprised to see we’ve offloaded.

Even before breaking ground, ideas are flying and challenges have mounted. That’s why it’s great to be supported by a team of like-minded experts – as we are – and why we’ve decided to share each and every step along the way with you, our amazing audience.

(00:01:41) #STRShareSunday: @richhollowretreat

  • The best time to start your listing’s social accounts
  • Initial plans for this brand new investment property 

(00:03:32) Recapping Our New Hocking Hills Cabin Project

(00:08:53) Now What? Getting Started with Reporting & Planning

  • We tracked: Rates, fees, pricing, reviews, FAQs,  and messaging 
  • Consistency and uniformity are key for comparison 
  • Determining planned scope of the listing (smaller units)
  • Quicker speed-to-market and ROI
  • Surprising reaction to photos being used in comparable listings
  • Prioritizing concept vs. costs  
  • Using AI tools in your vacation rental competitive analysis 
  • Preview of upcoming new-land episodes 

(00:15:54) Planning the Plot: Surveying Existing Buildings & Utilities 

  • Existing utilities were a huge positive 
  • Paying homage to the original owner’s caretaking
  • One cabin + two large garages + two sheds 
  • Bed that rolls under the kitchen (not a typo)
  • Rehabbing the existing cabin vs. building new ones 
  • Early considerations of nearby construction in the future 

(00:22:12) Important Steps We’ve Already Outsourced & Why

  • Sarah’s decision to outsource design of the cabin refresh 
  • Celebrating an incredible one-day cabin design (for $1,000!)
  • How Sarah prepped the Upwork listing just right 
  • How Annette is going about outsourcing the books

Download a transcript of this episode.




We are always preaching the virtues of making the jump and just getting started when it comes to launching your property’s social media presence. So, even though we haven’t broken ground just yet, our Instagram is up and running! We will be posting consistently and sharing our entire launch story – the good, the bad, and the funny – because, is it all even worth it if you can’t have a good time? So let’s get this party started. We hereby invite you, our beloved listeners, to follow the account and share any and all words of encouragement along the way! And thanks in advance for being a part of this new and challenging chapter in our shared journey as short-term rental hosts and investors.

We would love to feature YOU, so don’t forget to use #STRShareSunday to get your chance!

Together, Annette & Sarah are the dynamic duo behind the wildly popular podcast Thanks For Visiting, co-creators of the Hosting Business Mastery Method, & seasoned short-term-rental hosts.

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