Seeking Advice: Scaling STR Business vs. Starting a Glamping Venture

[Bradley Guion]

Hi everyone,

I'm a novice investor currently managing one short-term rental (STR) that's been performing well. The property sits on 5 acres, and after a successful first year with cash flow, I'm exploring ways to expand.

Initially, I considered building another home on the property to use as a second STR. However, I'm increasingly excited about starting a unique stays/glamping business. My vision includes developing the land into a destination with features like driveways, walking paths, utilities, and unique lodging structures.

Here’s my tentative plan

1. Place the existing STR in an LLC

2. 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?

• What challenges or surprises should I expect?

• Does this sound like a scalable and sustainable business model?

I’m also open to partnerships or collaborations if this aligns with anyone’s interests or expertise. Any advice or guidance would be greatly appreciated

Thank you in advance.

• Bradley