As far as I know there is no real problem, with a tail dragger, she even adopts the same attuide for landing as a tricycle undercarrige. They are a bit of a pain for taxieing thou'.
They were in use for training in the late '70's,and even later, so the present boss should be able to drive one, no bother, which is why I suspect that there is something else wrong wit the aircraft in question.