when i setup xboxes for my friends i always set pxhddloader as the default game copy utility. it's directory structure requirements suck eggs, but nothing beats it for one button game management. it will tell you how big the game in the drive is, how much space you have left, and lets you delete other games to make space with a single button - easy enough even for my stoner friends. most of these guys don't have/use computers, so ftp is straight out.
personally, i use qwix to copy games to my hdd and manage game w/ flashfxp.