Currently implementing Sharepoint - would love to find an OS alternate for this
One easy win is implementing more effective and open collaboration software than Sharepoint. It's a great document repository, but it sucks at pretty much anything else that I've ever seen anyone try to make it do. Might I suggest just firing up a web server and pushing out some new services? Have ye a wiki yet? What about other social networking software? If you don't have Office Communicator in the field, you could roll out an LDAP-authenticated Jabber system.
If you guys are heading in the collaborative technologies direction anyway, the above may be easy things to tack on in a related side project. Roll out Sharepoint, a new Wiki (possibly embedded into Sharepoint via iframes), and/or an IM service under a fancy n00b friendly moniker all at once. Seems like the sort of thing my employer would do - Obvious cons, obvious pros. Complicated rollout, potential big morale boost from rolling out something easier to use than Sharepoint or a Wiki ala an IM system. Get a positive "shucks, that was easy" from the customers that might bleed over into training on the more complicated parts of the rollout.
That said, I guess the key point would be to offer something new and not just change for change's sake. Most end users and management could care less what's on the backend. They want new but easy to use toys that help them increase productivity.