Re: Brings back bad memories
"Beyond that you implore your boss to tell their boss his users are not competent and need training / redeploying and its not his or your problem."
It depends. If it was your department's decision to replace the familiar with the unfamiliar then perhaps it is your problem.
But in general, use of the software is just part of the user's job so training the user to do their job including the software should be part of the user department and, although you might help with it, any written document should be the user department's work and cover the whole job instead of the IT aspect being taken out and documented separately.