I'd list it at the median, but it all depends on location. 

Moore - Given the age, the items you mentioned should be expected. 

I have done a cursory look at the May calendars of many VRBO and Airbnb listings, and it isn't uncommon to see NO bookings for May whatsoever. 

Every purchse needs to be made on a case by case basis, looking at everything from the area, current value (not to be confused with list price), future market value, income, expenses, et al. 

Other costs - need to examine item by item, and many will be subject to your accountant's interpretation.

I would list any major issues in the Summary and tell the buyer to read the entire report for minor issues, like GFIs, sticky windows, etc.

However how much are you spending is this even going to be noticeable to your bottom line, or would you be better focusing energy on other items?

Did they save the contact info for each booking so you can contact them with the new listing?

I sent a letter to the owner address listed in Alabama GIS, but they never responded. 

This might mean asking for personal guarantees or using assets like personal belongings, investments, or other valuable items as collateral, aside from the property being bought.