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I don't use outlook or trillian, but if neither has an export feature, why not just leave em' on your existing box while you still need em?
If your not currently a mac user, it's a bit unnerving to switch, things seem a little retarded at first, but after you get used to it it's actually alot better (In my humble opionion).
I say go from it, i recently converted from pc to mac and i haven't looked back. I have both xp and os x on this machine (using bootcamp to dual boot, and parrallels to use xp from within os x), and i haven't been into windows other then was neccessary for testing, etc.. since i got used to osx, and i have no plans on going back.
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