Tommyudo, restore the iPod to factory settings to fix it. Reload your music to the iPod, all will be good as new. You may want to try formatting your iPod for Mac. Mine behaved unpredictably when it was formatted for Windows.
I tried out the plugin tonight (2k, WA5, 2nd gen, 1.3, Mac) and had mixed results. For starters, the iPod loaded to the ML very quickly, much faster than with other softwares. WA was able to play songs from the iPod.
First things first, I thought, let's test it. So I deleted the contents of my iPod like I usually do when I'm updating it, and Winamp ceased to recognize it. I stopped the iPod, waited and reconnected but the iPod was thereafter unrecognizable to the ML. I couldn't reload the iPod without using other software, which I did.
No harm done.
p.s. I'm glad to see this plugin's gone open.
p.p.s. This is in regards to Barto's fixed version.