RE: Tail wheel trainer
I think it would be a good thing to try, but harder to learn at first. The ground-handling will be difficult for a student.
You can minimize the nose-over tendency by moving the mains forward a bit and you can have the student taxi with the wing off for practice.
Having moved to taildraggers several months ago, I think they are just as easy as trike gear. I don't see, NOW, what I was so afraid of THEN.
Maybe some instructors will have reasons for not doing it, but I can't seem to find one. As long as you can recover the plane if needed, go for it.