Everyone else uses a database-backed program that automatically organizes their collection (iTunes), and expects to synchronize from that database to their device. If you weren't so set on doing things the way you did them in 1998, you'd be fine with iTunes — it can automatically download the podcast files, and synchronize that playlist when you plug in the device to charge it.
Oh, and I would have to jailbreak iPhone to use it.
It will take the data from your MP3 Directory structure - lets say something like Artist/Album/song -- and automatically generate the correct tags for you.
BTW, maybe I'm missing something here but shouldn't it be possible to keep an index on the device and just update it when files are added/deleted?
Yeah, it's enabled by default but I'm pretty sure it's the correct behavior for most people.
Directories are, in a sense, high-maintenance indexes, but some of us find the existing tag system utterly inadequate and need to fall back to this solution.
Given an outside-generated MP3 (as opposed to one I ripped from CD), I had scripts that would look at the tags to figure out where to put the file in my directory hierarchy.
Said directory hierarchy would then be synced to the Archos, where it would be accessed via the file browser.
To this day, I still miss this approach when I want to listen to classical music. I felt like listening to Beethoven's 5th symphony a couple days ago at work, and it took me about 5 minutes to find it on my iPhone. It would have taken me 5 seconds on my old Archos. The iPhone/iPod pretty much falls apart when faced with music that doesn't fit into the genre/artist/album classification.