Converting file names from Mac to Windows.

I am an Apple tech at a university that uses both PCs and Macs. We have found that we run into some problems when transferring a user's data from one platform to the other.
When transferring lots of files, what do you experienced Mac techs use for safely converting file names from Mac to Windows?
From Windows to Mac?
We've tried NameCleaner and ended up with bad results.
Please let me know if there is something good out there for these conversions.
---Timothy

The problem looks like this:
1. User wants to switch from Mac to Windows.
2. We back up the data from his Mac to a server (an X-Serve RAID).
3. We log into the server from Windows.
4. We try to pull his data from the server.
During this data transfer, it quits with an error stating that it can't finish copying the data. I wish I had the exact text, but I don't. It does this repeatedly, and stops on different files from different locations.
In essence, without "cleaning" the Mac file names, data transfer to Windows cannot successfully complete. It quits on certain Mac file names. In the past, NameCleaner has worked sometimes, but now we have had some issues with NameCleaner (which don't matter in this discussion). The goal is to find a better solution than NameCleaner.

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