Generally, it auto-splits, but with songs that are cramped into one song on the CD for silence and sometimes, songs that have very complex silent gaps, the MD will NOT be able to split perfectly. You'll have to add a track marker manually later. No worries though - it shouldn't interrupt the gapless playback. As for iPods, I love the organisation now and how I can just enjoy the music much more quickly, but MD was a more DIY feel to music and for geeks, a LOT more entertaining. Nowaday, you should get a lot of looks on the trains and bus with MD. When I moved from Sweden to Canada in 2000, I was very surprised that very few people had them because MD was big in Sweden - at every audio shop and most of my mates had them.
When I was on the train in 2001-2 with my MD unit (and especially in 2006 when MP3 players were making it really big), people would come up to me and congratulate me on the cool device or just eyeball me. I had the Sharp MD-DR7 at that time in dark blue. Sexy beast.
