You can do this simply by adding the columns, and when the device is connected, then selecting all the books that are on it and changing the value of the column. You could use a yes/no column, but, I would probably use a single tag-like column and use a tag for each device. Then, when you get a new device (they seem to breed and like company) all you need to do is use a new tag.
But, you can automate this with the Reading List plugin. This allows you to create lists of books in different ways. One type is to populate the list when the device is connected. The list will get refreshed each time the device is connected. And you can have list specific to a device. One of the other features of the Reading List is to change a value in a column when a book is added or removed from the list. So, plugin the device, wait for the connection jobs to finish and the list is populated and value set.
I don't do this. My attitude is that if I want to know what is on a device I can look at the device. But, I make sure the books that I want on the device are on the device.
This also uses the Reading List plugin. One of the other types of list can be synced to a device I create one of these each of my devices. When I get a new book, or modify one, I add it to the lists for the devices that I want that book on. Then, I connect the device, the books are synced and the list is cleared. With this, I know that the books on the device are those that are supposed to be on the device.
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