Buying down the rate with points is a personal choice, but if you're holding the property long-term, it can definitely be worth it for more stable cash flow.

Creative financing is really how I am able to find cash flowing STRs for my buyers right now.. the margin is really low with DSCRs right now especially with taxes and insurance in FL.

Is insurance rate high? 

Laud area-Cash flow is minimal, $300 a month-Selling now would allow opening up of equity to redeploy in another market with over 2x the cash flow for a new build-New market won't appreciate as much as FL though (not even close)-Current home will likely get hit with higher taxes, insurance etc. in coming year and years to come-Biggest reason to consider just keeping current property?

I can think of a lot of funny responses to this statement but know this "it is the title company that decides if a property is insurable, no one else"Only they will tell you what you want to know if that particular quit claim deed is insurable.

What is the best way to assess and submit for claims with insurance with least resistance from the insurance company ( assuming it’s not a smooth process.

You cannot invest what you do not have.Initially before you invest, your success is measured by how much you have in (for instance) your Vanguard Money Market Fund, or an FDIC insured Money Market account, or stuffed inside your mattress, etc...

I'm self employed, no other "job"I have STR insurance policies that show a line item for Loss of Business Income.

If the investor fails to make payments, it could damage the seller’s credit, even if they've relinquished control of the property.Insurance Issues: A change in ownership might affect the property’s insurance policy.

It's an insurance policy that borderline applicants have to get if everything else checks out.