I've been to a couple legal offices where WP & DOS are still being used.
Since they don't really need anything other than very basic text editing (some line numbers, some strikeouts, etc) they don't see a compleling reason to move to Windows / Word / GUI.
Most touch typists don't / didn't like the idea of having to remove their hands from the keyboard to mess with the mouse. WP (actually, WordStar was better) put most of the frequently used key combinations on the home row + CTRL or ALT.
I usually suggest updating on the basis of support: i.e., "You know if that printer dies, there'll (probably) be no support for the new printer" (which, of course, depends on which printer is currently in use).
If the platform and application works for what you are trying to do, aside from a support angle, why upgrade? People can only type so fast, and (as a business manager friend once said) " All computers wait at the same speed."
I still have an old CP/M 8080/Z80 box around and working. Televideo terminal, Diablo 630 Daisy printer. WordStar, SuperCalc, BASIC 5.0 ....rocks right along on 64K of static RAM and dual 126K Floppies. It's kinda fun tinkering with the old stuff.
FWIW
Scott