Concepts like sub-to agreements or leasing to STR operators sound appealing but require careful consideration of the risks involved.

I don't know anything about their policyholder experience.However, every homeowners policy I've ever seen, even with a "home sharing" endorsement or rider, requires some owner use of the property. 

Flat out, I realize we're friends/family, but I need this lease in place to comply with laws that require things in writing and for my protection should there ever be issues.

Pay attention to the details and be organized Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

We recommend RentRedi for tenant and lease management. 

If you have a perfect closing and first 3 months your dreaming Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Some of the new laws in the state house will require you to provide Air-Conditioning.

Equity skimming requires an INTENT to defraud.  

In addition, the Grantor will probably be required to sign the same seller's affidavit that are needed for a non DIL closing. 

If you can qualify for conventional cash out refinancing, most lenders do not have a minimum loan amount requirement.