It seems like it would be fairly easy to add a button to the View Create/Edit Comment screen that would evaluate the columns in the view and for columns that are not calculated, pull the Comment associated with the Column in the source object. I would guess 80% of the columns in Views I create are not calculated, so being able to press a button and having the Comments imported from the source Tables/Views would be a big time saver. I would like it as an independent button and not run as part of the Auto-Add Columns button is on occasion I will want a slightly different comment on the Column in the View and after entering a new comment, I would not want it overwritten.
Let me know if this makes sense, or if you would like more information.