AIUI, wine is generally designed to work as a single-user set-up. Each user has their own virtual Windows configuration and programs to run. So yes, each user will have to have their own installation of the program.
For multi-user support, You might want to take a look at CodeWeavers' Crossover Linux
. I believe their professional versions add multi-user ability. I couldn't say for sure though.
Also, I assume you've ensured that you have the necessary licenses for everyone running MS Office?
If I were in charge however, (and depending on the situation), I think I'd simply tell everyone to just suck it up and learn how to use OO.o. It's not like it's all that
different from MSO, after all. Not to mention that being "uncomfortable" with a program is kind of a lame excuse anyway.