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tilia answered your last question perfectly.
In answer to your other two, yes your description is correct for the first and no there is no way to automatically add to a list based on a value in a column for the second. Calibre does not have the necessary "triggers" in place in its model to support such a behaviour.
I suggest you associate a keyboard shortcut with your add to list action, that way you have the fastest possible way to both add a book to your list and set the custom column all in one step. Then treat the column as "read-only" in terms of not editing it in your library, just think about putting stuff on/off your TBR list instead.
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