I haven't seen a mechanism to do what you want. It could be written as a plugin, but it would need either the drivers for the device to collect the timestamp info, or for the plugin to get the timestamp directly from the device. I don't remember if any of the drivers do the former, and the latter might need something written for each device.
The way I normally handle what you are doing is with Reading Lists. I have one Reading List per device. When I add or change a book, I add it to the RL for each device I want it on. For my main device, the RL syncs automatically when I connect. For the other devices, when I connect, I go through the list and decide if I still want the book on that device. I might not send it if I have already finished the book. I also use the list to update the read status.
The other thing I do is to sort the library by the modified timestamp while the device is connected. This shows what is and isn't on the device. I'll probably have a rough memory of when the device was last synced (my main device daily, the others a lot less often) and looking at what is and isn't on the device will tell me what I need to update.
Neither method is perfect, but it's close enough for my use.
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