Reinstalled OS, How To Re-sync ITunes & ITouch

Still working on my friend's laptop. I told him to backup all of his files, and specifically directed him to his iTunes Music folder. I then wiped his drive, etc.Now, he says... when the iTouch is plugged in, it should 1) "automatically" install iTunes from the iTouch, 2) the computer will then "remember" his name, settings, and iTouch serial number, 3) so that it can restore the library from all of the music, etc. from the iTouch-- 4) which is NOT the same as the iTunes Music folder, as there is much more on the iTouch that is not in that folder. Again, he tells me this NOW. *Note* The data files (ie iTunes Music folder) have not yet been moved back onto this drive.

1) I had already installed iTunes before I let him try to resync his iTouch. He insisted that me installing it before he plugged the iTouch in is one of the things that is causing this not to "work," so he uninstalled, redownloaded & reinstalled the new version anyway, iTunes 10.5, this morning.

2) He insists that, upon opening up the program the FIRST time, the computer "remembered" his name since it says "[name, name]'s Library" under Preferences. "That's cuz when I installed Windows 7, I put your username as the same that you had. It's just taking it from your username." "So, it remembered?" :facepalm: And he says, "All the settings are the same." "Well, then, you must have just happen to have had them set as the same thing that is default." After nearly 2 weeks, he does not understand what an operating system is or what "erasing everything on the drive so it is completely and utterly blank," means.

3) As for restoring the iTunes library from what is on his iTouch, I'm at a loss there. My first experience with iTunes ever was when a friend put his whole library on my new & empty iTunes, but that was back in 2006.

4) Is it even possible to sync things onto your iTouch without going through iTunes, when it is set up to only work with iTunes, so that the content ends up on the iTouch, but is somehow NOT under iTunes control & thus dumped into the iTunes Music folder? Now I'm just getting confused...