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For the music, I think you can transfer individually, but if the metadata says that two songs are in different albums you won't be able to play them one after another. When you're transferring, are you doing it from iTunes directly, or the actual files? Try the latter if you haven't, it might just be that iTunes doesn't know what to do with the reader as a drive.
If you're buying something from the Sony store, I'm pretty sure you have to go through the Reader software, unfortunately. Since you have a 950, if you want to buy something from Sony you could just buy it from the link on your reader, and then you can use Calibre to organize it with the rest of your books if you want to. If you have things from other sources (Kobo, or one of the infinite other ebook stores), there should be a way to authenticate them with ADE and use Calibre for organization and loading to the reader. If you have things that don't have any DRM, you can put them straight into Calibre.
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