Quote from @Dyllon Gibbs: Hi All,Does anyone have experience with rent guarantee insurance and any specific companies?

Proven Track Record – Experience in vacation rentals matters.

Additionally, related-party rules could disqualify the exchange unless ownership is structured correctly.

We're based in Tampa and, in addition to personally investing, I own a mortgage company that provides financing for tons of investors.

Since you and your husband bring 20+ years of residential construction experience to the table, you already have a huge advantage.

I would like to shadow anyone who is experience in this lane of investments.

Considering that, you are likely going to see appreciation year over year, which essentially will be additional equity you'd capture just by simply living in the home. 

Would help if you stated what questions you had so people could reply right away.I have knowledge on HELOANs but not direct experience.

You'll want to ask about their experience, read reviews, understand their availability, pricing, insurance / bonding, and how they safeguard their funds. 

If we had hundreds of loans out, we’d have enough monthly income to aggregate the payments into additional loans—but we don’t.If you do this, your note will have to have a compounding clause in it, provided by your lending attorney.