Another way to ease the migration is to deploy Windows ports of ssh and X servers, so that users run their Windows stations as dumb terminals. 'Dumb' only in the sense that it's the Linux box that executes the programs, while the X server takes careof managing the display on the local station.

On another, slightly related matter, I'll question why you have to take into account the users' familiarity with Linux. The judicious use of .rc, .profile, and other relevant files should enable a user to go straight into X, maybe at first with a standard window manager (I personally find KDE bloated, but then that was pre-1.x even), but, regardless of the choice of window manager, the standard applications should be readily and easily available.IOW, users shouldn't have to run vi to modify their menus -- that's the network admin's job.