The airlines that always had great balance sheets are DAL and LUV and they probably stand the best chance to sustain the least financial damage. 

Don’t earn a reputation of being that guy that doesn’t pay people who provide you a service.Regarding the buyer, if they don’t meet the timeline, you can walk away and begin the process all over again which will increase your carrying costs, though you may end up with the EMD.A better option if they pass the deadline may be to ask for a second deposit to make sure they’re serious about buying the property.

When I walk into a house, I can't tell if something needs replaced unless it is obviously damaged.

If they're problematic then that's worse than being unoccupied since they're probably going to do more damage and be more of a headache.

But, is there any risk of further damage if you don't? 

Then when you moved in, your fee would transfer to a damage deposit.

Helped a tenant for years and then on the way out conflict and about 5-8k in damage and two months of unpaid rent.

I don't trust them, they are incredibly rude, irresponsible and feel entitled I am really worried about them damaging the property and with everything happening it's nerve wracking.

Once you've checked everything, make a list of damages and anything that needs cleaning.For costs, you should know what it costs to clean and repair items.

They know which tenants have damaged previous rentals or who has been flaky.