The idea had been somewhat dormant, but I did get some new information this spring. The Laurier Centre (http://www.wlu.ca/lcmsds/index.html) was the source of mapping that I was aware of and they now have plans to make their collection available online. Their Archive page has a link that they will activate at some point. They were vague on timing, but it is something that is on their radar. This won't be as grand as I had contemplated (they will be basically just scanned documents, not GIS-ready files that I would like to see), but having the scans available will be a first step. I've had brief discussions with some of the staff there and hope I have planted a seed about some of the possibilities.
They have done some interesting work with their new Italy guidebook and with a new book on the North Shores by Marc Milner that demonstrate exactly the type of integration that I would like to see available to all kinds of researchers (base maps, war diary map references, Google maps, period airphotos, etc). Unfortunately, their work is very centered on desktop publishing tools, so that is their frame of reference. That results in great looking maps, but not data that anyone else can do much with. The idea of taking greater advantage of some of the more robust possibilities through GIS or the like is somewhat foreign to them.