I think here is where some of the confusion may lye...(pun intended)
my quote - emphasis added
Just wondering - are you trying to drag n drop from the Calibre database window?? I didn't think it would do that. Even if it does you wouldn't necessarily be getting the most current version if metadata/covers etc unless you "save to disk" first. If you right click on the title in Calibre you can select "open in folder" (or something like it) then drag from there to iTunes.
So...my point was that:
1) Dragging the ePub from the Calibre window
2) If you want to get the most current metadata/covers - that you may have changed/updated within Calibre - you need to save to disk first
3) From the Calibre window
right click and select "open in folder" to open a folder that you can
drag-n-drop to iTunes
My apologies for not being clearer.
Can we move on now?