Contactower -
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Anyone "learning to fly" and asking me "which plane to learn to fly first", I would answer "a taildragger" in any case. I believe the best airplanes would be DH-82 Tiger Moth, or Stampe SV-4 with an open cockpit... The Cubs and equivalent (Auster AOP6 class) are second best trainers.
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I realize 90% of the people now learn to fly in tricycle gear airplanes... and the transition from that type to taildragger requires most pilots some hours of dual instruction... I remember, having my taildragger PPL, getting qualified to fly a tri-gear C-150 required me to get... 45 minutes dual and 3 landings...
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A comparison (about learning to drive cars) -
Would you learn to drive first, with automatic transmission, or would you first learn to drive a car with a clutch and 4 or 5 speeds... same philosophy. How about an old MGA and learn to double clutch down to the first gear which was not synchronized...?
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All the best
Happy contrails