@Kraftwerk - It could be one of two things:
1) You need to add your device to your new installation of Calibre/Reading List. As @itimpi pointed out, this can be found within the Reading List customization on the Devices tab.
2) Many plug-ins (and I believe all of @kiwidude's) now store customization/config settings within the calibre DB. So if you see your device in the Reading List Devices tab, you may need to a) disconnect your device, b) remove the device from Reading List devices, c) reconnect your device and then d) add the device to Reading List devices. This is because the OS link to the physical device could be different between laptops/PCs, especially when you move from one OS version to another. So doing this will re-sync Reading List to the OS.
I had to do #2 when I switch from XP to Win 7.
Hope this helps.
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