About tailwheel aircraft – they are a FUN challenge!! (my opinion!) They DEMAND that you learn to properly use the RUDDER!! Or you may do a ‘ground-loop!’ How many pilots of piston engine aircraft DON’T properly use the rudder?? Far too many, in my experience teaching primary students!! Takeoffs and landings become more of a ‘fun’ challenge, especially with some wind. You will learn to ‘dance’ on the controls as you fly to stay properly ‘coordinated’. You will also become good at ‘slips’ to a landing, because some tailwheel aircraft do not have flaps.
Flying tailwheel aircraft does not require an additional ‘rating’, but a logbook endorsement IS required. Unless you have prior experience flying tailwheel aircraft before April 15, 1991. I learned to fly a tailwheel aircraft in 1979 shortly after earning my Private Pilot Certificate. I am now in a 4-way partnership in a 1953 Cessna 180, which is a lot of FUN to fly!! This keeps me tailwheel current!
Unfortunately, the way things are now, only a handful of schools in each state have tailwheel aircraft and a tailwheel instructor, as well. Most training aircraft now have a ‘nose wheel’ unless you fly an aerobatic airplane (Citabria or Decathlon). Also, because of their dwindling numbers, insurance generally has higher premiums for tailwheel aircraft.