Maybe it is more difficult if the damage was more serious like fire or flood but it goes same with any insurance claim.

Seller is the Agent.Seller bought property in January of 2023 for $730,000Current “As Is” Value : $770,000Target Acquisition Price: $730,000-$780,000 After Repaired Value: $900,000Repair Estimate: $120,000Initial Offer Amount: $715,000Loan Program: Bank Statement Program.Total Estimated Monthly Payments (Principal, Interest, Taxes, and Insurance) $5500/month (based on $770k purchase price)Estimated Gross Yearly Income from Short Term Rental: $160,000 (65% Occupancy, $700 a night| (STR Listing Comparable properties Listing 1 Listing 2 Listing 3)Net Monthly Income after management and taxes: $11,751.25Net Monthly Income after Mortgage Payments: $6251.25 ($75,015) Per YearTotal Cash Investment: $297,000 ($177,000 in down payment and closing costs and $120,000 in repairs)Average Yearly Return on Investment: 25% yearlyAverage increase in property value per year: 5%Average increase in booking revenue per year 7.5%Property Value average after 10 years: $1.5 millionTotal Cash received over 10 years: $1.3 million.Total Equity multiple min over 10 years: 6x total return on $297,000 invested.

Also, this would only remove the mortgage debt itself from your DTI if it was to work; you would still be hit with a liability for the annual taxes, insurance, and HOA fees (but also receive the benefit of the rental income).

Homeowners will always pay more than investors, and the easiest way to get the property in front of the masses fast is to list it. 

“What about medical insurance?”

Leverage technology early and put everything in the cloud, so you can access info wherever you are.Make sure to get properly licensed and obtain E&O Insurance.

However, you would not be able to get title insurance

I am seeing a different insurance issue.  

I guess a flat seasonal fee like any insurance policy, sometimes you win, sometimes you lose.

Insurance for what?