well that was helpful.
what about copying the layer, pasting in a new document, do your Arbitrary rotation, then pasting the layer back in the old document? I know its not perfect, but at least its a solution.
EDIT: OK went into PS and actually tried that...
thats a pain in the arse.
so the way I would do it is like you said.
do your Arbitrary rotation with your ruler... take the value and copy it. hit cancel.
then go Edit>Free transform and enter the value in the angle box at the top.
viola!
2 extra steps but works nicely. So yes, as far as I can tell, you have to manually do it.
but what the hell do I know I'm just a hack.