I also use plugboards to organize my books on all my readers, especially on the Kindle where you can't organize by Collections without doing it all manually (and that definitely just ain't gonna happen, not ever).
In Calibre Preferences, under the Import/Export section, go to Metadata plugboards, and add new plugboard. Enter azw3 for format, and Kindle2 for device. Under Source template enter the following with Destination field set to "title":
{series} {series_index:0>2s|[|]} {title}
Then when books are transferred to your PW2 they will appear as Series Name [##] Book Title, such as:
Jack Howard [03] The Lost Tomb.
You can of course change the order between the series, # and title to anything you prefer, but I find sorting by series name to be the easiest for me to find the next book in a series.
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