It sounds like you would like to get some money by getting a second mortgage on the house? 

As far as who's going to pay, it sounds like you will either have AC if you pay, or won't if you don't.

Hi, @Austin Mallette.Welcome to BiggerPockets.It sounds like you and Blake have done some good research and learning already.  

On the other hand, the renters are buying that investment for me... but 27 more years is a damn long time for that to payoff.As far as selling, we owe $235 and the same realtor told me it would sell for $285k to $295.So now as I'm thinking about it, getting ~$40k immediately by selling is sounding better and better.I guess the third option... rent it for a few years while the market hopefully keeps going up, and sell it while the place still seems nice and new.I would greatly appreciate any insights, thoughts, advice....

@Matt Brechting sounds like we are peas from the same pod, just separated by a few years!!

I have never been to Massachusetts so I cannot be sure about anything but you sound like you have planned out a new option that will work.  

Sounds like you are well on your way to victory!

Sounds like you have the right flow going.

Also the idea of using chair rail and wainscoting sound great.Good luck with the flip.

Sounds like you're already headed in the right direction, taking action!