Well I'll tell you what. I am probably going to get some really negative feedback here, but what the hell. I am a 'tough love' administrator.
So, what was my solution to my "Outlook" users? I didn't import squat except for contacts, including my own email history. Lead by example right?
I like the saying, "It's e-mail, not rocket science."
Most people have a load of crap stored up over years in their POP3 clients anyway in my opinion. I imported contacts and left their POP3 clients intact for "reference", when they wanted to look back and "see what I sent" etc.
After a few weeks, enough history is built up in their webmail client that these reference checks become fewer and farther between. I can't remember the last time I checked my old POP3 client for an old message.
And I saved myself a big headache and Gigabytes of disk space that would have been wasted with 'x' number of years of e-mail history.
"Let's look at this from a standpoint of "Status". What exactly, on the Space Craft, IS working?"
-Flight Control, Apollo 13