Comment git-annex assistant (Score 1) 272
"go easy on the 'just apt-get FubarPackageInstaller.gzip and rd -m Arglebargle' stuff"...
So why is he asking Slashdot?
Seriously, git-annex assistant might be the solution for part of his problem. assistant is a pretty front end to git-annex which uses git to sync repositories of file metadata and several other means (rsync, etc) to schlep the files between repositories. It won't run on his Windows box but does run on OS X and might be easy enough for his wife to use.