Today after speaking in person with the Executive Director of the historical society, she said they have a couple of lawyers on the board. They should be able to help me draft a property release that is favorable to them, the property owners, and to me. So that's the route I will go. I'm not looking to profit off of the images but want to retain the copyright. The historical society will have a free commercial license allowing usage for images of the properties they oversee. And I'd like the property owners to have free personal usage of their own property images (although not commercial usage). Only the images used for the calendar will be released unless this doesn't become an annual project. If that's the case, then each party will receive all the images. These are the terms that I want to be in place.
Some of you might be wondering why I'm even offering to do this. In the past I've found I grow exponentially with my photo editing capabilities when I do this type of project, and for a long time I've felt as though I've gotten stale. Plus I really enjoy taking photos of architecture which is something I just haven't done much on my own.