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It is "convoluted and ridiculous" because you need some way of telling the plugin which collections specific books should go into.
You don't "send a book to a collection", you "send an ebook file to an ereader device mounted as an external USB Mass Storage device".
Manipulating the ondevice content tracking database in order to tag a book as belonging to a certain collection, is an entirely different action altogether.
This can be done automatically on the Kobo (the functionality is built into the Kobo device driver), and it can automatically create collections based on e.g. tags.
The Kindle requires a plugin, and on touchscreen devices, the Kindle jailbreak and a hack running locally on the Kindle (since Amazon keeps the Content Catalog where collections are registered, in the rootfs where calibre can't see it).
It is pretty easy, really, all you need to do is tell KC which metadata column to use for collections, and then add the collections you want to create as tags in that column (you can reuse the bultin tags column if you want).
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