I finally took a break around lunch to setup my iPod. Unfortunately due to a stupid conflict I can't load all my songs on it at once. (For some reason my blue and white G3 unmounts my external firewire drive every time I plug in the iPod, it may be an issue of two bus-powered devices at once or something. I have to load about a gig and a half of songs onto my internal drive, unplug the firewire drive, plug in the iPod and copy, then repeat.)
I've got 3.2 days worth of music loaded so far, so I should be okay at the gym tonight.