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It's more complicated than "last one in the list". The only Kobo plugin that you can install from the plugin list that's relevant to sending books to the device is KoboTouchExtended, which calibre will always use if it's installed and enabled. You can't really even say "use KoboTouchExtended for these books but not these"; the closest you can come requires a lot of changing settings and restarting calibre and selecting specific books each time.
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