IMO if you don't have an iPhone the LAST program I'd be using is iTunes, it's a pig of a system.
Have a look at WinAmp,
http://www.winamp.com/ it's free & is really easy to use, you simple load your music & then use the drag & drop principle to add & remove music to your MP3 player. I use this onmy old iPod but unfortunately it's not compatible with the new iPhone upgrades so I'm stuck with crappy iTunes...