I like the Multi-level "cut 'n paste" idea. The Blackberry clipboard is of type Object, which means it can hold an array of Strings. I put together a quick test and it works. The only real problems I am having are that I can't find a way to modify the default copy command or add a context sensitive menu item to all BB apps.
For my test, I settled on adding items to the system menu: MultiCopy and MultiPaste (I guess I should add MultiCut too). This is an ugly hack though, because it means these menu items show up absolutely everywhere when you click the trackwheel, not just when you are in select mode or about to paste. Does anyone have any ideas on how to implement a system wide context sensitive menu?
Screenshots: Here they show up in the phone app where they should not be. Add here's a screenshot of the paste dialog showing 5 available items.