I own a 10 Gig Ipod (3rd generation). The poster above made a great point about accessories but there are "generics" everywhere for much cheaper. For my money having owned a cheapo 256, an Iriver, and an Ipod...The Ipod is dominant. In this case you really do get what you pay for. '98 will work but I wouldn't get an Ipod if you have to stay with '98. The software won't exactly play nicely if you know what I mean. I would personally suggest that new Ipod nano. Really a great machine and 1,000 songs is pretty darn good. Trust me, you don't need a 40 gig unless you own every song ever recorded.