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Have you checked out Rockbox? (http://www.rockbox.org/) I'm not sure it does what you're looking for, but presumably would accommodate the "competent hacker" you reference. I have a feeling you'll find the user interface lacking in some way, but it'll be a good reminder that open source projects aren't necessarily the paneca you suggest they are in your post.
Also, I'm not necessarily suggesting that Apple should turn iTunes into a full-blown open source project. I think the Darwin/Safari model would be a pretty good fit here: controlled by Apple but with outside contributions welcome. Apple engineers would still do most of the work, but they wouldn't be shutting out people who have valuable ideas to contribute.
Switching logic based on the state of the player when you plug it in is more complicated than you might think.
Oh, and your second comment about not kicking off syncing automatically? My guess is that it's to prevent people from unplugging the player in the middle of a sync they don't know is happening and causing data loss or some kind of unknown state on the player. Yeah, you could have iTunes overtake focus on the screen, but it'd be doing it all the time if you had a lot of Podcasts.
Good UI design is harder than it looks!
I don't really see your point about Safari; the open source contributions on that project (so far as I understand) are to generate a standard-compliant rendering engine, which is more of an objective challenge than the subjective challenge of UI design. Your iPod issues you mention are probably not so much an issue with programming man-hours as they are with sound interface design. I'm sure Apple engineers have a variety of channels with which to gather feedback on product features. I hate to generalize, but based on their existing body of work open source programmers would be just about the last group I would turn to for UI advice.
A more annoying issue with podcasts for me is how they are listed under the 'Artists' menu. I get around this by marking all my podcasts as compilations and setting my iPod not to display compilation albums under artists.
From what I've seen, iPods with iTunes do a better job of handling podcasts than any other mp3 player but I'd be interested to know if I'm wrong about this.