This is most like to be a fault in MusicMatch JukeBox, or an uncompatibility with Windows 98 SE
Because, nowadays most of the 3rd party software are targetting to be compatible or be "designed for" with Windows XP, I see the support with older Windows OSes are not good as before. E.g. ACDSee 4 and 5 has trouble installing in Windows 98, and you need to have the latest Windows Installer.
Next time try to install Windows XP (as you config is pretty good for Windows XP, i wonder why u don't) and I am pretty sure it will work for you. Good Luck!
