whoever told you this is stupid. you cant turn that setting on if your itunes isnt working.
when you plug your ipod in and the screen comes up that tells you that its syncing and what not, down near the bottom there are four check boxes; open itunes when this ipod is connected, sync only checked songs and videos, manually manage, music and videos, and enable disk use.
when you click manually manage music and click apply (bottom right corner of itunes) you just go to your music library, in itunes, find the music that you want, then drag it to your ipod under "Devices" all of this in the left hand pane of itunes.
as for your itunes not working, it could be a registry error. download ccleaner
http://www.download.com/CCleaner/3000-2144_4-10315544.html?tag=lst-1
run the cleaner then clean up the registry. dont be afraid of messing anything up, it is VERY easy to use and wont harm your computer.
if that doesnt work try downloading tune up utilities
www.tune-up.com
download the trial, its fully functional. run the 1 click maintenance. it should fix it all up. if that still doesnt work try an uninstaller. ive tried revo uninstaller and i loved it.
download that here:
http://www.download.com/Revo-Uninstaller/3000-2096_4-10687648.html?tag=lst-1
if you do use the revo uninstaller run the ccleaner afterwards to clean stuff up. then restart your computer and run ccleaner once again just to be sure everything is gone. go to apples website and download itunes again and it should all be good.
if none of this works then i suppose youll have to contact apple support, i havent found them to be much help but you can try.
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