I had Outlook and the Desktop Manager on Vista.
I would give it a shot if it makes your life easier and that is what you want to do.. Once it's setup it shouldn't break.
outlook will be your primary PIM manager for Contacts/Calendar/Notes/Tasks, so once you get use to Outlook and the sync is setup you should be fine.
As far as the Desktop Manager, you can use 4.5, 4.6, or 4.7 their really isn't too much different from those three. So you can use 4.5 if you don't want to take the "risk" with 4.7, choice is up to you.
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8830 -> 8330 -> 9550 -> 9650
Just think about how far BlackBerries have come from then till now... And what else is coming.
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