Tenant took photos and videos but nothing detailed - a single shot or two of a room from the entrance, so is saying fridge was fine, normal wear etc Next - If we are being nice and deducting ‘portions’ of the charges and tenant continues to grind away, or this goes to court, do the compromise and smaller amounts offered negate the full amounts that could have been charged

Maybe she will sell for less, but I suspect you'll have to convince her that she benefits from the transaction somehow.Usually, a title company expects a written purchase and sale agreement first, before they will do a title report and they need to know the sales price in order to set the coverage.

Anything that nice, I'd rather just manage it myself and make way more than their master lease. 

My clients are able to find pretty nice cash flow! 

3.Draft a written agreement where the property owner retains full ownership of all guest funds (nightly rates, cleaning fees, and taxes), while the cohost invoices for management fees and reimbursable expenses?

It isn't jumping out of the plane that hurts, in fact it's a pretty nice view, it's hitting the ground that does the damage. 

For example, most real estate deals throw off significant depreciation which can provide a very nice short to medium-term tax shielding benefit.

It would be nice if you had a contact who was an actual mason not a marketer.  1930's construction is rare so maybe they cut some corners it was a global depression.  

Although insulating the floor is a nice extra, it is not the primary way that cold gets into the house.

And if construction doesn't start up soon and return to precovid growth, you're going to see a nice gap that helps drive occupancies even a little further up until it does.