Flying a tail wheel airplane is no where as difficult as many pilots make it out to be.
It is all about recognizing yaw and controlling it before it starts to become a problem controlling it.
When I teach pilots how to fly tail wheel airplanes I make sure they can control it on the ground at all speeds from slow taxi to high speed runs down the runway with the tail in the air.
When they are comfortable with direction control on the ground we go flying.