I have been watching the steady decline of the purchase and it is stating to get my attention.

I am paying attention to this very closely as that will affect my pocket book directly.

Pay attention to some details like revolving debt, total balances, and their ability to make on-time payments (if the screening service provides you as much detail). 

I'm going to be facing a lot of medical expenses within the coming years so I'd love to be able to put this money I have to use in shorter term options in real estate. 

I usually advise people to not go to college unless they are pursuing Medical, Law, Accounting, Finance, or MBA.

I've rented to people with bad credit who I believed would be good tenants and were, a couple who had a medical expense bankruptcy for one.

Photos Don't Match The PropertyIt may be tempting to use stock photos or highly altered photos of your listing in order to get more attention online, however this is one of the quickest ways to irritate your guests.

Find someone qualified to look at this type of home and don't cheap out; a good inspection can save you a ton up-front and over time.Also pay close attention to the foundation (assuming it's a rubble/stone/brink foundation) to ensure that its straight, not bowing or seeping water. 

Did the underwriter just bring this to your attention? 

Again, in MA you would quite likely be on the hook for a lifetime of medical expenses.