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Here's how I handle the importing you're referring to in 1:
All of my ebooks have a tag of "processed" -- it used to be just a regular tag, but since 0.7.x, I've added a "workflow" column and put it and other non-content-related tags in there. I also have a saved search for books that do not have a "processed" tag. So, when I add new books to my calibre library, I click on that saved search and a list of all the books I just added comes up. I can then fix up their metadata the way I like it, finishing off with giving them a "processed" tag ... at which point, of course, they vanish from the not-processed view.
It sounds more complicated than it is. It's a really straightforward way to keep track of which books I've massaged and which I haven't. Now that calibre can compare the list of books on my 505 and mark the ones that need to be loaded, it's even easier than ever. I also have a "DNU" (for "do not upload") tag, so I also have a saved search for books that are not on the reader and aren't tagged "DNU", for easy updating.
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