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I think synchronizing media via softwares like iTunes is by far superior to simple drag'n'drop because you can let it sync everything or just specific playlists and even smart playlists automatically. You also can use iTunes' intelligent media organization based on meta tags instead of having to rely on old-style folder management.
That said, this method has also downsides, especially for the iPhone. The iPod is for music and videos only so I don't see a problem there. With the iPhone however you may want to use it more like a mini computer and may want to transfer files different than those iTunes supports. I agree that it's a shame you can't even transfer text documents or PDF files to the iPhone. The workaround to email those files to yourself to be able to view them on your phone is pathetic.
So I think iTunes should be able to transfer files other than multimedia as well. Preferably via an additional tab in the iPhone view where you could just select folders or even single files to watch and sync. Meaning that whenever something is dropped in that selected folder, iTunes automatically syncs it the next time the iPhone is connected. Of course the question would be how to manage those files on the iPhone, e.g. throw them all in one folder or organizing them in some kind.
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