Especially when you look at balancing the risks such as new NY Renter Laws, high taxes, and lack of business growth.I think there is upside with the new hospital opening up soon, Marist adding a medical teaching program, easy access to metro north, favorable pro-growth government, etc..I've run some #'s for Poughkeepsie and nothing seemed to cash-flow enough for the risk, however, I've not dug deep into off-market deals, which is where you are going to have to look.I've pretty much given you a non-answer...

It is in the medical center and it is in a fancier area of town.

All my cash is tied up in a property that would make a great AirBnb or mid-term rental, close to hospitals and medical schools in central Phoenix.  

In my past career I was a Respiratory Therapist, the most under appreciated and mischaracterized/labelled medical professional out there, so I guess I'm used to poor press? 

Everyone in the house with have a medical condition,  most notably asthma when the air goes out and they will move out without notice.  

Shortly after, my wife and I encountered some pretty hefty medical bills which I am working to pay off in the next 3-4 months.Here is my dilemma. 

Our TOD properties are getting sold at $1,200-1,600 per SF, but that's typical to high profile buyers at tech/medical companies that make 8 figures a year and their typical bonuses can cash buy these types of properties. 

Oh, and BTW, I had to pay the outstanding bills out of the money that we got, so without the reno, they really would have gotten soooo much less because there were extensive medical bills. 

A short list:Liability- Bodily injury and property damage, medical paymentsProperty- the dwelling, optional contents coverage (un fixed appliances), loss of rents.Insurance policies are considered contacts of adhesion..

He sounds like he would not make a good tenant (he's banking on getting a job in the area but doesn't have it yet) but he brought up an issue we hadn't considered:  outstanding medical debt.