I’ve experienced success in the STR market here in St Pete myself but I’ve since transitioned my properties to long term rentals for convenience and time management sake.

Once that phase is complete, I’d transition back into long-term holds.As for the cash-out refi, without at least doubling the rent, I’d be in a net-negative position each month, which doesn’t seem like a worthwhile trade-off.On the tenant side, I agree with your point about the business aspect—it’s something I’m working on coming to terms with.

Keep in mind all these markets are very different than the Cambridge area in terms of tenant base, household income, transit, etc.Happy to connect if you'd like to chat more!

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?

While cohosting is my initial step, my goal is to transition into a full-service hospitality management company as the business grows.

I could see really getting into this and wanting to keep growing the number of properties I own so long as I can keep qualifying for loans, so I need to understand how to transition away from the VA loans once I'm maxed entitlement and keep growing my portfolio.So it's build up equity then huh, and refinance out of the VA loan or cashout to buy on another loan type?

A bit strange that you leased the commercial spaces knowing you would be pursuing a conversion but understand the objective of taking out your capital partner and I see in your follow up post the relocation language so you clearly thought through the transitional phase.

The the transition was seamless and since I know the tenants already had to pass their screening process, I was not concerned about inheriting these tenants.

It's essential to prioritize their comfort and peace of mind during the transition.● Management Company Challenges.

If you are still with CR of Maryland they will transition you to their management system.