- Itunes can't be used with third party devices.
- Itunes doesn't save artwork correctly in metadata so that it can be read by third party software/devices.
- Itunes isn't as customizable as Foobar, Mediamonkey, or Musicbee.
- Itunes can't use VST plugins.
- Itunes can't add music to other people's Apple devices.
- Itunes doesn't support FLAC.
- Itunes can't be used with Rockboxed Apple devices.
These are the top seven reasons why I personally don't use Itunes, the artwork issue being a major one. Musicbee is by far the most functional and easiest to use for me. It will convert artwork to a specified size when copying to a third party device. The tagging and auto-organization features are so easy, fast and powerful it makes other programs look slow and buggy. It's as sleek as iTunes and has great skins to choose from.
After using Mediamonkey, Foobar and Winamp extensively I have to say that Musicbee is by far the best option, with Foobar in second.