SteveG
I'm not sure I follow. What I mean is that MC is correctly 'guessing' which files I want it to send, because when I confirm the transfer, the only files being sent are the ones I've added to the playlist since the last transfer (ie the 100 MB of files from my earlier example).
So, MC does 'know' that it needs to send only 100 MB of files to the handheld and not 2100 MB, furthermore it knows that 2 GB of its 4 GB capacity is still free. Therefore, why does it report that the capacity is 100 MB short for the selected files, rather than proceeding with transfer and then reporting 1.9 GB free space remaining?
(For simplicity 1 GB = 1000 MB)
BTW, I am using one playlist to contain all of the files that I want to exist on my handheld. I have also added a view scheme under my main library that only shows items from this playlist. That way I get a nice interface to create and update my 4 GB selection of files that I want on my handheld, by selecting albums in the pane view and checking/unchecking the playlist from the Action Window. It works great - except for the spurious over-capacity warning I get each time.