I finally took the step into the 21st century music-listening by moving my music collection, previously spread out over two harddrives, to an external drive and letting iTunes handle the library.
The biggest difference is that I listen to music a lot more often now. It's just easier to load up iTunes and having it on random play than thinking what I want to listen to, navigating to the correct folder and then dropping it on the playlist of the player app. (The one I used previously didn't have a library feature.) Having thousands of songs available a click away is somehow a really powerful feeling.
The second biggest difference in my listening is that I listen to fewer albums now. Previously I'd drop a whole album folder on the playlist, play that and repeat if I wanted to listen to something more. With the random play feature I listen to a lot fewer full albums.
Having delegated the position of music-player to iTunes, I also tried its encoder, which was quite a shock. Having done my encodings to MP3 using the LAME front-end LameBrain, it always took me quite a while to rip a CD. But the LameBrain was last updated, wait for it... 4 years ago, to the day, yesterday. So the tech in it might have been a bit old. Using iTunes was incredibly snappy in encoding in comparison. I'm really itching to rip some more just to have more accessible, I can really see now how people end up ripping all their CDs. Perhaps after the prices go a bit lower I'll buy a new HD and swap out the old 160GB in the LaCie Porsche FW (which might be interesting since they seem like a bit of a challenge to take apart).