There is one issue I'm having with Winamp, and I'm sure it stems from my iPod being a Shuffle. I can't really identify how it's deciding to arrange the songs on my iPod, but it's probably the order that I put them on there. the iPod Shuffle isn't designed to use playlists, it just plays the songs in order or on shuffle.
The problem is, Winamp lists the songs on it by artist, not the order they appear on the iPod. I also see no way to rearrange them once they're on the iPod, which iTunes allows you to do just by dragging them up or down. I tried creating a playlist on the iPod, but that didn't work. The only way I was able to make sure the songs got on there in the order I wanted them was to make a local playlist, then right click it and do "send to Wyre's iPod". Since my USB doesn't seem to be working as 2.0, this took close to an hour.