It sounds like you’re in a great position to get started—$100k saved up and a clear goal are huge advantages.

Both groups are showing up with a clear purpose, need a good night's rest and want a safe place to live close to where they work/study. 

My vision includes developing the land into a destination with features like driveways, walking paths, utilities, and unique lodging structures.Here’s my tentative plan1.Place the existing STR in an LLC2.Apply for an SBA small business loan to fund the next steps, including a feasibility study (~$10k+), land clearing, and infrastructure development.While this direction excites me, I’m torn between pursuing this venture and continuing with a more traditional approach—buying one home per year using conventional loans.I’d love to hear your thoughts:•Has anyone transitioned from STRs to glamping or similar ventures?

Diving into creative financing options like you’ve done shows initiative, and you're clearly thinking about the big picture.

From my experience, success in real estate investing starts with clearly defining your goals and continuously educating yourself through podcasts, books, forums, and courses.

This will give you a clear idea of what the house might be missing, and or need and gives you time to make those changes/additions before your first group.Another tip: I think it is natural for bigger properties to have more vacancies during the week/slow season.

Make it clear that you'll only pay when that person signs off on work done.

Good luckI must have not communicated clearly.

I see that I wasn't clear in my description of our current situation and our goals. 

But he has clear advantage of getting much larger deposit (landlord in most jurisdictions is limited to collecting 1.5 or 2 months' rent payment, which he must place in an escrow vs. $8000-$10000 Scott can collect and use for any purpose the next day).