RE: Tri-cycle or Tail Dragger?
I find that neither one is harder than the other. Different to taxi cause you taxi the tail dragger with up elevator. Landings are the same.
So i'll answer your question with a question. What is it that you really want to fly. A warbird? perhaps a large bomber? or a 3 D aerobatic job Whatever is your fantasy plane fly that type, ie warbird get a tail dragger. etc
Oh by the way if you havent got a fantasy airplane. fly the opposite of what you have now. It'll make you a better stick (pilot)