I have thought about this before and its a great idea in concept and it just might be in Brawl but as of now, we know nothing based on how item switch works in Brawl. It might be changed up in Brawl like the coin machine has been turned into a shooter. As well as the many other things that have received refinements or utter changes in Brawl.
However, personally, I doubt that item switch will be as detailed as you imagine and dream it to be but you never know. I think an item switch update on the Dojo would be nice as its something that hasn't been spoken about in Brawl much in detail. I'm sure, many average and professional players are eager to hear about it. We will probably have to wait for Japanese release though accompanied by leaks to attain such information though till we get the game.
Anyway, welcome to Smash Boards.