You can also take advantage of lower down payment loan products rather than going 20-25% down on a conventional investment loan. 

Lastly, know that any conventional loan likely has a 'due on sale' clause, where if you change the title of the property, they can call your note due.

Conventional.

Would like to do owner occ conventional with 5% down but don’t think we will qualify.

This pretty much wipes out any conventional lender. 

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?

House hacking is an excellent strategy, and just got a lot easier as conventional loans now allow 2-4 units with only a 5% down payment.

I know the cost associated with a DSCR is much higher than with a Conventional loan but the commercial zoning may be problematic for Conventional.

Happy Thanksgiving Rick, Go the conventional route.

Exhaust all of your conventional or government financing options before you get into DSCR.