The house had new vinyl siding but it covered up rotted T1-11 siding, like literally the nails were attached to air.

I have thought about air bnb for short term rental but it wont be my first go to.

Money or not, this is what you're going to have to deal with by prolonging the relationship.Also, if someone can afford a luxury $4k rental (for example), they should be collectible for any amounts owed for breaking the lease early.

getting knee deep in Air bnb offers in several cities.

REally difficult to make Air BNB work here now. 

We are working to add air conditioner or heat pump to 15 new 14'x56' homes in SC. 

Frank, i'd likely stay closer geographically to your future investments, when you start investing in property outside of your local area you'll realize that air travel becomes a real issue.

Central air through out and zone heat.

My primary residence out here at Twin Lakes has had some serious Air B and B traffic only problem is it's my primary residence.

I live in England and have found a property that would offer a good Air BnB income.The seller's realtor is saying that he can get Air BNB receipts from the current owner to prove the income.