It sounds bizarre, but most tenants (a) don't know how cheap the insurance is and never ask; (2) have been turned down for insurance in past because of poor credit and so don't like to risk being embarrassed, so never apply; and/or (3) made monthly insurance payments, missed a payment, were cancelled, nothing bad happened, and ended up feeling like they wasted their money. 

They might be just as embarrassed for having you out to clean up soap.More than anything, I am surprised your home warranty did anything to help. 

Just a question that I’m to embarrassed to ask.

But since your misconfidence is to such an embarrassing degree, not to mention borderline belligerent, what I think you should do is go out and make a big leveraged bet with your own money, not someone else's, on one of your predictions.If it works, keep rinsing and repeating- but don't forget the with your own money only part.Lol so in your world, everyone must be there own Doctor because it is "hubris" for a person who spends there career as an informed expert, to say what something looks to be and what a person should try to do for it. 

Moreover, however, I am embarrassed and appalled as a Realtor that this individual would ask for anything from you since 1) it is a short term rental that you advertised no fee paid and they didn't ask first, and 2) you are doing that person a favor by accepting a short term rental in their clients' time of need and most likely desperation.

Remember, If your offer is not embarrassing, it may be to high

Why bring up the most embarrassing part of their lives as a total stranger? 

@Gainet Mata - a generic suggestion is to start making offers, even if they seem embarrassing to make.

I'm embarrassed to say that I never knew you could post images to these forums.  

The most important things you need to know is.......How to find your deal - power prospecting - distressed properties - ugly houses - sellers with problems - houses with problems.Next - how to negotiate - some investors say "If the seller doesn't cry - your offer is too high".You also have to be prepared with a well designed contract of sale that gives you -----Right of possession - disclosures to assign your contract -Full Disclosures - a profit disclosures - assignment disclosure - and a an important clauses to say what happens if you can't find an assignee and you have to walk away without a profit while the seller looks at you very disappointed - make sure you don't embarrass yourself using unproved flip techniques - get it right the first  time, get educated on the right way to do a flip deal.