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?

You don't want to give any reason to shut the door on the conversation, you're goal is to elicit interest. 

Secure contracts with sellers at lower market pricing, then connect with cash purchasers eager to pay more, earning from the difference.

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!  

Are you able to do the cost seg or paying someone else? 

Take into account you will be paying medical.Other???