Together the portfolio is worth 2.5 Million and he STRs them on Vrbo and Air BnB. 

The air conditioning doesn’t work, the fridge is broken, and the property is far from "turnkey."

I would say air on the side of caution.  

The second option is that she go to court, where she will lose, you get a judgment for everything owed including cleaning and repairs, and then you send her to collections where it will prevent her from qualifying for another rental, getting a car loan, etc.

To be clear, we inherited the house, but there is a complication that prevents us from being able to sell it for a few years, but we will eventually sell.

For prospects seeking to rent many months in advance we are typically declining those and seeking to lease up as close as possible to the next available date so as to prevent potential gap periods that will be harder to lease. 

They built a pole barn structure, air conditioned it, strung up some lights and trendy decor and host baby showers or weddings almost every weekend. 

I always got the impression that he had a bad criminal record or never got his high school diploma/ GED equivalent or some other issue was preventing him from getting a license, because he was basically just brokering without a license but calling it consulting (I don't know any of that to be true for the record, that was just the impression that I got from his comments and might explain why he used a fake name?). 

The wholesaler won't disclose any issues that the property has that could prevent them from getting paid.

Putting the acceptance criteria prominently in the ad will prevent most of the non-qualified people from coming to the open house or applying.