Calibre has a "Yes/No" column type, so you can just add that (Preference, Add your own column). Then your father can use the arrow yes to select the book and then the column. Pressing F2 will edit it and use the up/down arrows to choose yes or no.
But, I'll also make my usual suggestion at this point... the Reading List plugin.
With this, you can create a list of books. You can create one that will automatically send the books to the device. The plugin supports keystrokes to add the books to a reading list or view the list.
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