Can Excel automatically do what I'm talking about, without any further intervention from me? (i.e., not running a macro and not copy/paste/manual-drag-to-fill operations)
When inserting a new column, you seem to want Excel to read your mind about which cells, of the new column are to be left blank, which should be copied from the adjacent column.
Ain't gonna happen unless you write a macro to do the dirty work.
This is starting to sound like you may need to create an excel form for data entry. Fill in the new values, hit the button. Excel processes this adding a column and filling it in.
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