RIght now, the homeowner market is red hot so flipping is a good way to make some very nice medium-term profits.

I have only done long term rentals, but I know other investors doing short and medium term rentals (medium term generally renting to travel nurses at Johns Hopkins, University of Maryland Medical Center, Mercy Hospital, etc.). 

From what we see on this forum, FF is more suited to what you are doing which is closer to Medium Term Rentals.

I am waiting & hoping to see how the market improves in Pittsfield - they've been putting a lot of money into the city and recently, the Tyler Street corridor, so I'm hoping that medium term, the property values will rise.  

Can't say specially without knowing all the details of this specific place.If there is a medium-sized population center nearby, it is likely that it'll be partially booked in the winter as well by non-vacationers. 

I'm currently working on a property to turn into a short / medium term rental.

Perhaps if you shared what your medium/long-term goals are we could help a bit more.

I was just hoping there was a new medium that exists that can replace insurance and easily give us peace of mind at a low cost. :) 

Trulia shows pockets of low, medium, and high crime in both areas, and really good deals that are in each area.

We have an LLC, we operate medium term rentals in the building.Unfortunately, it’s becoming increasingly difficult to work with him.