I suppose it's true that our modern aviation world has very few tailwheel aircraft and as a result fewer people have the opportunity to fly and instruct on them. However, I have seen some very experienced pilots sweating bullets and trying to save face while trying to keep the sharp end pointing down the runway!
Flying taildraggers definitely requires more skill as you have to pay attention to what's going on. I have taught many people to fly taildraggers after completing their licences on a tricycle gear aircraft. Most people commented it was like learning to fly all over again.
I have been very fortunate to have flown many types of aircraft and helicopters but my favourite is my own pride and joy; a 1946 PA12 Super Cruiser. This is a rather docile little machine compared to a Piper Pacer. All taildraggers exhibit similar characteristics on landing and take-off but some can really get your attention! I have flown both the piston and turbine DC3's and the TP's are by far the more demanding with the use of reverse thrust. The PZL M18 Dromader, used for fire-bombing amongst other things, is a big heavy 1000hp radial monster that flies ok but can bite on the landing. The Ayres Turbo Thrush is a rocket ship when the hopper is empty but is a delight to fly. The saddest thing for me was when Cessna stopped building 185's !!
Getting back to the thread; I think a lot of people talk about tailwheel aircraft from a position of ignorance. They are not inherently difficult to fly. The insurance companies are obvious proof that people are afraid of taildraggers as they tend to wince and squirm when you mention any form of training.
At my home airport in South Africa we have a good number of tailwheel aircaft resident and in regular use. At least they are still cheap and fun to fly.
