Turned out that my problem with Winamp not recognizing my iPod was corrected simply by using a different plugin. ml_iPod still has some kinks to work out; I lost all my playlists after installation. That's easily corrected - the only one I wanted to keep was the Steve Earle "Train 'a Comin' 'Winter Harvest' sequencing" playlist (anyone who owns the original Winter Harvest Records release of "Train 'a Comin'" knows what I'm talking about). It's a small price to pay as long as I don't lose my songs automatically.
Additionally, I managed to transfer all of my iTunes podcast subscriptions to Winamp's Shoutcast subscription service. Even "This American Life." What this means is that I might never have to fire up iTunes again. Unless I find some radio streams to transfer.
Thank you, Winamp.