iTunes was always crap. I run the Windows version. It has inconsistent menus, disappearing menus, a different user interface on each page, a sync button here, an important checkbox there — overall an outstanding example of poor UI design.
My iTunes got corrupted and for years the text labels on most of the buttons and menu items were invisible. Some kind of font issue, I guess. I tried uninstalling, reinstalling, fiddling with Windows fonts, nothing helped. Fortunately, I remembered where the sync button was. That was all I needed, most of the time.
Then the computer that I had iTunes installed on conked out. I fixed the computer and installed a new hard drive and reinstalled Win 7 and iTunes. Works great but now it turns out that syncing doesn’t really mean syncing. I’m not sure what it means. All I know is that after I do it the file libraries on my iPod and iTunes don’t match. You can get them to match but only at the cost of deleting all of the files on your device. You cannot download files from your device to iTunes and add them to any new files you’ve acquired. It’s obvious why this is the case: Apple wants to keep people from busting the DRM on purchased files by downloading them to unauthorized computers. But Apple’s system makes life difficult for anyone who has a significant file library and replaces or upgrades his computer. There are workarounds but they are mostly a PITA for the user, and particularly for the non-tech-savvy user who replaces his hard drive or computer. This is a case where the customer doesn’t come first (though, to be fair, Apple is far from the only company that does things in this way).