First I use tag database tool which does rename files (with reversible .bat) but it fails in the second phase while trying to create the database, complaining about an error reading some mp3 file (like td5.mp3) which doesn't exist anywhere on the system (the name of the mp3 sometimes varies as well). So I have to run another tool - iHP tool? the one with the GUI anyhow - which will accept all now shortened filenames and create a proper database. On their own neither tool will work. Also, 52 char limit was supposed to be removed as of last week or so according to some posts I've seen on iriver forums, but only if you use 3v2 tags. Unfortunately it still doesn't work for me so I'm not sure if that is some kind of beta that's not officially released.
By the way the unit is troublesome both on my windows 2000 computer as well as on my windows xp pro laptop. On XP I cannot get the drive to show in the explorer, or it gets there for a split second then goes away. If you manually type the drive letter in the url bar then it works but it still never gets displayed in the left pane navigation. I have this sometimes with my portable hdd unit too - seems to be a bug in windows xp. Also, trying to properly disconnect the unit by ordering the device to stop through the tray icon doesn't work more than half of the time, even with all the windows refering to the drive closed, so you're forced to just unplug it anyway (this happens with iPod on win2000 as well, even though it's firewire, but much less often).