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The book has to be on the device and matched to the book in the library. That means that when the device is connected there is a green tick in the "On device" column.
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I do have the green ticks.
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The book is not a purchased book that has been downloaded to the device from Kobo. If it is, you need to use the option to allow the driver or plugin to update the metadata for purchased books. But, I don't recommend this as the changed might be over-ridden when you sync with Kobo.
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The vast majority of the books are sideloaded, including all the ones with series.
Ultimately, I started getting some strange behavior from the Kobo where books were getting lost and the wrong screensaver kept appearing, which I think was related to having KoboTouchExtended installed. I could only rectify it with a factory reset, after which the standard steps you laid out finally worked. I'll report back if it doesn't work after a firmware update. Thanks for your help.