My manager has a BB8800 which he would like to create categories on and sync back to Outlook.

Is this possible?

It appears he is able to see the categories from Outlook to the BB, but can it go the other way when creating on the BB and see on his Outlook desktop?

Yes, the categories will sync to/from BB/Outlook with your contacts.

"Group" addresses will not sync back to Outlook.

Will an upcoming BB OS include meeting category support?

It would be a lot easier to create those categories and maintain them in Outlook, because the outbound category sync (and optionally filtering) is rock solid

What are you asking, the BB already suuports category sync to the Outlook.

There are no categories in meetings on a blackberry with the current 4.5.x.x OS. When will the BBOS support categories for meetings in the calendar.

I don't know when they will be included in the calendar for meetings.