I don’t listen to music on my PC I listen to music on the iPod.
On the iPod I have smart playlists (which will update on the ipod in the same way as they will on the PC) set up that play songs that I haven’t listened to in a while from various different genres. I can therefore decide what genre I want to listen to and be sure that I’m going to hear something that I like and that I haven’t heard recently allowing me to rediscover old favourites.
If you manually copy over only a few hundred songs at a time you will end up listening to the same stuff over and over again, and if you are going to do that you might as well use a portable CD player and get better sound quality.
What makes the iPod great is that it allows you to listen to your music in different ways.