To see the series information on Your Kobo You must plug again Your Kobo to Your PC with calibre working, not to send the book again. It is different.
You send the book, then exit Kobo, plug in again and when You exit You will see series information (if You want to it immediately). You have to configure the plugin to update metadata on device.
see:
Kobo icon>driver>configure current driver>metadata on device and advanced
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