I don't think a tail wheel airplane is much more difficult than a nose wheel plane in nearly any aspect of flight, just as a float plane is pretty similar to a land plane in most (but not all) aspects of flight.
It's the take off and especially landing - most especially cross wind landings that make the TW more challenging.
I'd like one because I want to put tundra tires on it an land on unimproved strips. That said, there are some tricycle planes with monstrous tires that allegedly are as good as TW for that. 3 bladed props help the tri-gear plane with clearance.
It's still, sadly, not all that hard to put a TW on it's nose if you don't handle it well on the ground.
Nearly (certainly not all) TW are high wing, which kind of preselects. A person who hated high wing wouldn't have a tail wheel (in most cases - and there is not a large selection that work well in the rough terrain mode).
I wonder how many who prefer TW have airports with multiple runways so they can minimize cross wind and/or have grass strips which are more forgiving?
A little, tandem TW is next on my list of planes to get to base off my farm.