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Frustrations With ITunes

Please do let me know if I’m doing some obviously wrong, but I’ve got a bit of an issue with iTunes that I can’t solve without using a workaround.
I have iTunes on a work computer (ahem – don’t tell our IT department) and also on a home PC. I like to listen to podcasts. I understand that iTunes will only sync to podcasts on one PC, so I’ve chosen my home machine. But sometimes I like to download an up to date podcast to listen to on the way home.
I can’t sync to my work machine, but I can drag and drop individual podcasts from iTunes to my iPod. Except that the tracks then don’t show up under the iPod’s Music or Podcasts (or Audiobooks) menus in iTunes. They’ve vanished – even though I saw some transfer activity as I drag and dropped.
Not only that, but you can only find these orphaned “songs” under the Songs menu on the iPod itself. In other words – they’re there on the device, but you can’t see them via iTunes.
That’s a bit of a problem, because in Apple’s infinite wisdom, it seems to have neglected to include a “Delete” function for songs. I quite like to delete podcasts after I’ve heard them to keep things nice and tidy, and I’m not always near a PC to do this.
But now I have audio on my iPod that I can’t see through iTunes and can’t delete on the iPod. My Nano could quickly fill up this way.
My workaround is a little program called Yamipod which seems to let me explore my iPod directly, find these orphaned podcasts, and delete them.
I guess it’s a bug, and searching Apple’s forums suggests that I’m not the first to have this issue. Suggestions included starting afresh by restoring my iPod to factory settings! Except that some of my “music” (in particular Audiobooks), I’ve archived off to hard drives to keep my PC clean. Plus, that’s not a very neat solution is it?
And while I’m at it, why is it so hard to rip spoken words CDs and have them displayed as Audiobooks? If you buy an audiobook on iTunes or through Audible things are fine, but I tend to either have mp3s to transfer or CDs to rip. The only route seems to be renaming files as *.m4b rather than *.m4a files and “deleting” the music files while re-importing the folder with the *.m4b files. The reason that I want to have Audiobooks separately managed is that it keeps the menus clean for when I’m looking to listen to either spoken word or music, and it ensures that I don’t have chapters of books turning up mid-shuffle. Audiobooks also automatically bookmark where you’ve got to. Actually, Audiobooks is a bit of a mess with all the chapters placed into a single folder rather than being able to choose “Titles” and then “Chapters”. And yes, I do “Join Tracks” when I rip a CD to minimise chapter points.
I’ve only recently started to use iTunes fully by linking it to an actual iPod, so I’m a bit surprised that some relatively basic things are so complicated to achieve considering Apple seems to release new versions of iTunes on a very regular basis. This isn’t all just because I’m using Windows is it? Is all sweetness and light in OS X?

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