iTunes is terrible. What should I be using in place of it to manage all of my songs and transfer them to and from my iPod?
I currently use Floola: http://www.floola.com/modules/wiwimod/
Another good program is Sharepod: http://www.getsharepod.com/ but the drag-and-drop feature didn’t work in Vista, I don’t know if they have fixed it
But I recommend to first back up all data from your ipod because these programs can sometimes mess up the database.
I use the ml_ipod plugin for Winamp. (The built-in iPod support in Winamp is Not Good.) It still sucks in some ways. E.g., doesn’t preserve album order and filenames in creating playlists and the playlist name is munged when syncing and has to be fixed each time.
Of course this is for MS-Win OSes, which may not apply to you. (Ahem.)
Are you on a Mac or PC?
I use and love Windows Media Player; I use the dopisp plugin to transfer tunes to my iPod. It makes the iPod appear like any other good MP3 player in WMP and you can then sync it effortlessly.
Sorry, I wasn’t able to get on the board today to respond to my own thread. I’m using Windows XP.