Here in my office I have 4 computers on carts that we roll around the building to classrooms and conference rooms as needed. I try to keep them all as similar as I can, system-wise, but people often put their personal files on any one machine (and change them frequently.) They then need to get that machine each and every time they need a computer; this of course leads to horrendous scheduling conflicts. Is there any software that can be installed on these machines that will copy alll of these files across the network automatically? I envision a system such that, each time one of them is turned on, it looks across the network to see if any of the others are on, and if so, it compares a certain list of files, and automatically updates so each has the most current copy? This way any changes on any one machine would sooner or later migrate to all of them, and anyone can use any machine and have a high probability that all of their current files will be available.
I haven’t used it myself, but Unison looks like it might work for you.
If it’s not too many people, it would be far easier to just give them each a flash drive to store their files on. 256MB drives can be had for $10.
I use Synctoy, one of the free Microsoft Powertoy utilities to synchronize files from my C: drive to an external hard drive. But in your case, have you considered moving the users’ My Documents folders to a network share, so they’ll see the same files no matter which computer they’re on?
I would look at source control software… They are generally meant for managine source code in programming projects but I beleive things like TortoiseSVN will also do alot of what your after.