In the meantime, we would like to open up a written dialogue (via email here) as to the fairness of charging us full rent until the weatherization can happen.

For most it's just a way to open dialogue for some kind of workout.If it went to court would they win?

I've read most of the replies and they are getting away from the original post (but still in interesting and helpful dialogue).I started out working with people like @Jeff Rabinowitz that financed me on deals based on the deal itself.  

This will open the dialogue. 

Regardless, if moot with the bank, you need to protect yourself from outsiders zeroing in on the deal once you start work or the owner having other ideas.The bank ultimately will have the typical process when it comes to shortsale or application (qualifying to be unqualified) which can range on average three to six months and sometimes shorter or longer.You will have to retrieve all info from seller and as much paperwork as possible after you have signed a contract and most importantly, a Authorization to Release Information (which will allow you to dialogue with the bank).The bank will retrieve a Broker Price Opinion (BPO) of the home and in essence see if in fact is upside down to even do a shortsale.

All kidding aside, I work with all GCs to make sure that both of us are completely comfortable with each other and try to have an open and honest dialogue in the very beginning to try (the best we can) to avoid any pitfalls or misunderstandings.At the end of the day, when all work is complete, I can say that most every time I'm satisfied with their work and their satisfied with the fact that I paid them promptly.

Even without working the numbers it didn't seem like a "deal" but I thought I'd present to the experts to start a dialogue.

I think I voted like 5 or 6 times to responses, I don't know if you guys caught it or not but I thought there was a lot of lessons to be learned in the dialogue within these posts.

Finally Fellas,Now I am feeling better that we have some positive dialogue going...

As a newbie, still in the education phase, I guess my biggest fear is actually meeting with a seller and communicating in "real estate dialogue."