I highly recommend initial training on taildragger, if you can find one! The student will learn the skill to fly it, and everything else will seem easier after that. All of their flying will better for it, not just the runway work. While flying a Twin Otter with a pilot new to me, he asked if I flew taildragger a lot. I replied that I did, why did he ask? "Because you use the pedals!"
The student should learn taildragger while they can, imagine that like a manual transmission, taildraggers will become rare in the "public" world. It's going to end up that unless you either own a taildragger, or can borrow one, you simply won't have an opportunity to fly one at all. Get the experience while you can...
Good to see you back here Sam....