Is the old machine running OS 8 your only machine. If it is then you are stuck with older rippers and you won't get the rippers with the new codec (mp3 crusher or something, new is better I guess) But if you had a new machine then I would rip and then transfer.
But back before iTunes I use to use Audio Catalyst which was nice, did your standard rip and a sort in folders. There should be a host of free players Vamp always a fun one. WinAmp, maybe
But do check the versiontracker.com alway the best source of info