Syncing iTunes Library on Portable Hard Drive at Home and at Work

I have my iTunes Library (including my music, videos, ringtones, podcasts and audiobooks) stored on a portable drive so that I can play my music at home and at work. Now I have a 3G iPhone and synching is causing me problems.
I have always manually copied and deleted music and videos from my iPods because I like that level of control. But the iPhone isn't as intuitive. I turned off syncing on my iPhone for everything but the Apps (because I cannot drag and drop them onto my iPhone in the Devices list of iTunes). And those I am syncing manually by telling iTunes to sync the Apps when I click the sync button (this is the one located on the Applications screen when I choose my iPhone in the devices list).
But today I am at work and I am being told that I am not authorized to use this iPhone on this computer so I cannot sync my Apps. Well, it's the exact same iTunes library. Why is this an issue? I sometimes need to adjust or copy things on my iPhone in two locations. What's the big deal?
A second problem is my Podcasts. For some reason, I cannot copy my Podcasts to my iPhone easily. I have many Podcasts that I collect in my iTunes library and I occasionally want to copy select ones to my iPhone. With an iPod, I'd just copy it over and it would appear in a list of Podcasts. With my iPhone, I have to copy the file to a playlist on my iPhone, and the Podcast doesn't show up in the list of Podcasts underneath my iPhone device. They don't even show up in the list of Music under my iPhone device. I am not even sure I am really deleting the files once I delete them from the playlist on my iPhone. They disappear, but I don't know if I am getting that space back because they aren't listed anywhere else on my iPhone.
Sync problem three... when I try to sync my Apps, the iPhone tries to back itself up to my computer. I click the little "X" button on the iTunes display and the backup stops and the Apps start to update. But I have already deleted the iPhone from the list of "iPhones and iPods backed up to this computer" underneath the Syncing panel of the iTunes preferences and this keeps happening.
I just need my iPhone to be as easy to use as my iPod when it comes to moving content onto it. And it's not. I am forced into this synching scenario and it's not working to my satisfaction. I am feeling "Microsofted" by Apple here... as in, they seem to think they know what I want to do better than I do, and they're trying to make it "easy" for the average user at the expense of my wish for complete control. (I haven't even gotten to my horror of being forced to use iPhoto to manage my photos... I just haven't had the strength to tackle that mountain of potential issues yet... gotta work all this out first)
As a side note, if it's of any value, I have "Disable syncing for iPods and iPhone" turned ON in my iTunes preferences, "Sync only checked songs and videos" turned OFF on my iPhone splash screen, and "Manually manage music and videos" turned ON on my iPhone splash screen.
Helllllllllp!
Thank you.

christopher rigby1 wrote:
You must maintain the actual library files separately on the Mac and PC as they are different formats, and use different file paths for each song.
That is what I was hoping to avoid. That means I would not be able to sync my iPhone on both machines. It also means I would have to sync my libraries on a regular basis.
My primary goal was to be able to put a movie or two and/or a couple of training videos on the iPhone and when I get through them, be able to update the iPhone with new ones to use on the flight back home.
What about keeping the library files for both machines on the external drive, in addition to the actual library. Would that solve my problem?

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