So unless they really need to sell and they believe they wont incur further costs getting you to pay or taking the property back when you don’t.

There are times to pay down debt, but certainly not while you are trying to grow. 

Background context:I have a 805 credit score, low DTI and attempting to secure the lowest cash out refi to pay off a debt ($50k).

The roofer gets up on the roof and finds wind damage , and then the homeowner files a claim and the insurance company pays for a new roof less the deductable .Then after they pay for a new roof , you drop them and get another insurance company . 

Wouldn't all the cashflow go towards paying back my private capital lender?

They might even not pay if it is found out that you have been STRing the place and have a claim NOT related to guests.Ask your agent for quotes on STR insurance.

It's up to the Owner of the property to make that decision, but generally speaking most of our properties come with a washer/dryer, and the Tenants know that if there is any maintenance needed on it, they will be the ones to pay for it.

As far as doing a conventional loan, your only changes would be paying something off to lower your DTI. 

And I understand (I think) your making interest only payments until you pay back the loan?

With those documents in hand, you likely have all the information needed to share with your insurer, to identify who would pay for each part of the necessary repairs on your claim.Hope that helps!