It will also likely leave me with a vacant house in the winter which will probably be difficult to fill.

"Run Forest, run."

Addressing the problems is like trying to put out small individual fires in a forest that is burning.

I even looked Upstate, but decided didn't want to deal with winter weather and Property taxes in general in NY state are high..

Good getaway i guess too for winter.

The majority of this is really just trying to through buckets of water, on a forest fire of a market.

I want to be able to keep my house above freezing in the winter if they can't pay their oil bill.

I want to be able to acquire several more of these especially as my market goes into the winter and prices tend to drop. 

you are too much into thr deal and your not a real estate agent which is very illegali am a property locator i specialize in wholesale contract properties for home flippers or for estate agent that want to invest with an intent to hold for rental propertiesi simply use wat my investors want specifically in a contract and property  i communicate with the owner or contract holder and try my best to let them know hey this is what a potential buyer wants their contract to look like and so forthif they agree then i step out and give them conract information to my flipper or invester and that's it i am done with the  transaction.my investers pay me for the information of a potential property for them before they even see the property or get any information about the property..

We would basically be there in the winter and here in Maine in the summer/fall (June-Octoberish).It has a decent airport with lots of flights to Atlanta (my wife travels a lot for her job and uses Delta).