[JiveTurkey]

1. you aren't making a connection duplex by selecting multiple files at once - they are just going to be put into a queue and moved in sequence either way

2. hmm generally in computing - yes when you delete something it is very hard to delete every last file it used but this is mostly because of the tight integration with Windows files.
I would think that an Xbox drive gets fragmented just like any other computer but I have yet to see a program just to defrag it. I think the OS is small and efficient and even with games on your drive you probably dont move a lot of files around on it anyway.

So my conclusion is: if you add and delete games on and off it regularly you might want to do it regularly but if youre like me and only put a few favorites on it fragmentation is gonna be minor.