Find me a Linux distro where the 10 year old version is considered better than the newest version by 90% of the users; and the new versions are avoided by non-Luddite companies such as Intel.
Seems only someone with Ballmer's management skills can accomplish such a feat.
I agree, you might try contacting someplace like David Rumsey Historical Map Collection to see if they would be interested in helping, or might otherwise make recommendations.
A collection of other links that might be of interest:
Historical Map Web Sites
You might not be able to push a new server and new ways of working, but perhaps you could push a new service. Look into dropbox, and try selling it as backup, revision control, remote access, and the ability to easily transfer files with clients. Don't sell it as a fix to the son's problems, but a way for him to be productive outside the office as well as in. Appeal to the company being left behind technically if they don't start using cloud services for backup and revision control (with dropbox, the files will be backed up on Amazon's EC2 servers.) It runs on Mac, Linux, and even Windows, so all the systems can utilize the tool.
I would also spend some time working on my resume.
The most important early product on the way to developing a good product is an imperfect version.
