One way to demonstrate to these people before immersing them in a new OS and applications is to give them a trial run. The Knoppix live CD distribution allows you to give them a no-risk way to evaluate the environment and open their documents before reaching the point of no return. The Knoppix Linux distribution would be a good way to go about the first phase of the transition procession. Knoppix allows them to boot their PCs from a CD and try the Linux operating system and applications without interrupting their Windows installations. Also, it might allow for some of the objectors to become champions of the new Linux desktop. The thing that many people don't realize is that the cost in migration may be the disruption to everyday business and lost productivity. Finding ways to minimize that disruption is key, making sure that you partner with your users rather than dictate to them as the IT authority is a good first step. I would guess that once they see the new system, realize it doesn't suffer from viruses and crashes, and find out that the same tasks can be accomplished they will be happier and so will the IT staff.
There may be some potential hiccups with an OpenOffice.org migration with regards to formatting and macros. Microsoft Office macros are written in VB Script which Open Office doesn't support. However, the OpenOffice.org suite does have the ability to script actions using its own macro language. Also, more complex documents with indices and table of contents might not translate from one format to another. Depending on the enterprise this may not be a problem or could be cause for objection.
Also, you may want to consider implementing a document standard that directs users on what are appropriate file formats for different types of documents. By default, OpenOffice.org saves in its own format. However, it can still save in Microsoft Office formats. Making sure that OpenOffice.org users use the Microsoft format will limit interoperability issues with legacy Microsoft Office users. Also, it may be advisable to do an organization-wide Microsoft Office-to-OpenOffice.org migration first. OpenOffice.org runs on both Linux and Windows, and moving Windows users to OpenOffice.org before moving them to Linux could level out the disruptions when you migrate them to Linux desktops.
As for the best way to get them up and running quickly, you may want to consider a thin-client approach, where the Linux sessions are running from a server over a network to the current PCs which can be converted to thin clients or "dumb terminals." This way, you can stage their new desktop sessions in one place and then simply switch over in a matter of minutes. A good example of how to do this is using the Linux Terminal Server Project. That way you can extend the usable hardware life of desktop PCs and minimize disruption.
The thing you are doing right is asking questions before you make a mistake. With a well-thought-out plan, I think you have little to fear.
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