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Collections do apply to the 300 as well.
When you are in Calibre and adding tags are you adding just one tag per book or multiple tags? If adding multiple, each tag will need to be separated by a comma. If you add tags in Calibre I don't know why they would not show up when transferring using Calibre.
In the Sony library, once your Reader is connected look at the left hand pane and locate the Collections folder under Reader. Click on Collections then click the '+' sign in the bottom left corner of the screen. This will add a new collection and you can rename whatever you want. The process of putting books in a collection is drag and drop from the Sony library to the Reader then drag and drop from the Reader to a Collection.
A single book can be in multiple collections but there will only be one book on the device.
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