I completely agree with your approach to private money lending.

Are there any tax or management benefits to this approach?

We not only lost our hard-earned money but on top of everything, our health suffered, I had several sleepless nights due to the stress and anxiety that this horrible experience created for my wife and me.After the buy-back was completed, I approached Maverick to at least help us with our losses by requesting us to give back ~$6000.

Best of luck on your journey—your approach is strong, and with persistence, you’ll be well on your way to achieving your goals!

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?

Choose a multifamily or single-family investment approach, consider low cash flow priority, and monitor interest rates and seasonal timing.

Our house and land are special, so not worried about selling those in say 15 years or my son can keep.With Cash being King, I use a Buyers' market approach down there. 

I appreciate your ready-fire-aim approach, @Brendan Duggan, but you’re likely creating loans that might only be saleable at a discount.

Very wrong approach!

So you have that approach as well.