What about a 3rd option to allow the user to do a quick search for categories? Once people use the system for a little while they will pretty much know what categories they need to add. I think it would help adoption of the tool if people could quickly add categories.
You can see a demo of what I'm talking about here:
Click the popup button under Pick Multiple Names From Address Book
I am envisioning something like the left colum being each individual category and the right being the path to the category.
ie: Requirements Document | IT > Development > Requirement Document.
Also, has there been any thought about adding category selection to the Add Content Wizard and making the Create Content Dialog a wizard with the same option as OTB behavior in 3.0?
This uses tree views and has category search with result tabs as well as drag-and-drop (left to right column) to add categories to files. You can log on with demo1 + demo1, then click on [img]http://nexuit.net/nexuit_purple2.gif[/img] to go to the ajax ui.
