Then speak with property managers and/or Realtors who specialize in STR.I happen to be both in my local market of Tampa, FL. 

You’re speaking my language!

Speaking of, one of the reasons why they're behind is because of debt coming due later this year.

It’s a good idea to speak directly with an insurance agent who understands multi-unit properties to customize coverage for your specific situation.

I have never had to file a claim though so I can't speak to that experience. 

This would result in the veteran's entitlement being encumbered meaning the veteran only has partial, or possibly no entitlement remaining ie they might not be able to use their entitlement again until the loan is paid off.

However, consider calling the VA’s regional loan center or speaking with a VA-approved lender who can interpret the rules in a more specific scenario tailored for you.

Pretty much everything I have seen and read is:Find out the sellers motivation/problem and speak to solving that issue.Give an offer but explain how you got your numbers.Other than that, it seems pretty limited for negotiating information. 

Maybe they are only six months in and don't have any real experience to speak of.

Quote from @Phillip Austin: There are two alternatives to a security deposit, which I speak about in my book.