Lawrence,
There is much that can be said here. Excuse me for being long-winded. Your preliminary layouts look great. Let me start by telling you how much I appreciate your work on this. I would assume many others feel the way. I only speak for myself in what follows though. Aside from addressing a major longstanding shortcoming of AC, you might be initiating a productive process that could lead to other significant improvements in the program.
A couple of points about work flow and the letter writer (henceforth, LW). Excuse me if some of what I am stating is obvious.
In my mind, the LW is a combination LW and note printer. The interface for the two functions is currently joined (which is fine, but not necessary).
It is important for the LW and note writer to open as each note is signed off.
The LW is accessible by right-clicking on the patient in the main patient list, in the scheduler, and in the message list: also all important.
One feature of the note writer is the ability to alter the content of the note and its format (SOAP note or detailed note, with various headers). I think it is important to retain that feature. Print preview and default options are also important. Ability to print addenda and messages is nice, but not essential (they can be printed elsewhere).
The ability to select the patient or a contact from the Rolodex (or other contact manager, if you have a better one) would be important. I also might like a "To Whom It May Concern" option, though this could be free texted. I see little need for the "Patients" and "Other" selections. These choices could take the form of the radio buttons as in your example. On the other hand, you could just have one "To" drop down with "patient" as the first choice, "to whom it may concern" as the second, and Rolodex contacts below that.
The ability to format the letter as indicated in your prototype is a key feature. We really would like to print letters (and notes) that appear to be on our own "stationery". The other check boxes you show seem appropriate. I would also love to see the ability to set (and change) many defaults, or at least a "last used" memory feature. This includes the "include patient demos" and "include CCD" boxes.
The current LW mandates some things some of us don't like: automatic use of the patient's first name in the salutation, a fixed closing with fixed spacing for the signature line. The latter cannot even be erased and changed.
Ability to template and save to the chart are important features to be retained.
Again, this is just my two cents. Thanks again for all of your efforts. If this plays out well, I would be happy to work towards helping you obtain some compensation for your efforts.
