If you change folder names or file names in Windows Explorer, iTunes will not work for you, period.
You mean if i alter something already synced up? Because I know that. When i alter file names and folders, thats all pre-game baby. Once its uploaded to itunes, i just use the sorting options to tweak everything one last time and then i'm done.
Example:
-I download both albums by The Advantage
-Create a folder under iTunes/iTunes Music for "Advantage, The"
-create subfolders for "01 The Advantage (2004)" & "02 Elf-Titled (20006)"
-be sure to rename tracks in the format of "01 [track name]" in each folder
-upload to iTunes
-Change sort Album names to add "01" and "02" respectively in order to display albums chronologically
-sync
i know its a long annoying process, but its something i choose to do to keep everything organized to my liking. I've invested too much time for my massive library to suddenly switch to a 3rd party software option, but on top of that my computers such a peice of crap lately that i'm having trouble installing any new programs.
I recently heard of something called "tuneup" that is supposed to fix all this ****, but simply being unable to download it, i heard its a paid service. Why would I want to pay for that when I already do it on my down time? just not worth it.