Upgrading will be easy, The vbPortal core is bacically finished, upgrades will be modular, because of all the addons and hacks.
I have no idea at this point as far as vBulletin 3.0 and how big of an upgrade for vbPortal that will be, I do know there will be big changes in the calendar and that will affect the frontpage small calendar. Hopefully we will be able to get some help to figure that out.
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