Of course part of the problem these days is finding someone with enough experience in both Mac OS 8/9 and Mac OS X. Having someone knowledgeable in these areas can really smooth over the transition. There are Mac specialist almost everywhere.
That really is something that would be best trouble shot in person. There could be a conflict with those preferences and the new Microsoft User Data folder that was created the first time you ran Outlook in Classic. And as such also keeps some data in the System Folder's Preferences folder. Part of the problem may be the fact that while Outlook keeps a lot of data in that Microsoft User Data folder, it is still (at it's heart) a Mac OS 9 app. I usually set up my clients transition so to avoid these types of things.
