Tailwheel training is available to any pilot who has a current flight review, and who has reasonably current experience. I’ve elected to not try and get "rusty pilots" back flying, mostly because it would take too much time and I feel the value in that situation would be out of proportion to the expense incurred by the pilot.
As to what is included in tailwheel instruction, it is broken into a number of major sections. They are :
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Ground Instruction - This is about an hour to hour and a half of discussion covering the details of tailwheel flying. The dynamics regarding what makes a tailwheel plane different from the familiar tri-gear plane are explained in detail.
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Cockpit Familiarization - This is a short, but critical, piece of training. Due to the fact that the Super Decathlon is a tandem seat airplane, and due to the fact that critical controls can not be reached from the back seat, it is crucial that the front seat pilot (the student) understand all the controls.
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Ground Handling - In other words, learning how to taxi. There are nuances around handling a tailwheel aircraft on the ground that must be mastered prior to flying. This includes both slow-speed taxi practice, tight-maneuvering practice, then fast taxi practice on the runway ultimately leading to tail-up fast taxi practice.
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Familiarization Flight - This is an initial flight that gives the student a chance to learn how the Super Decathlon handles. We’ll do turns (including steep turns), slow flight, stalls, and flight at airspeeds used in the pattern and on landing.
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Three-Point Landings - This is the landing style that everyone starts with, as it is closest to how tri-gear planes are landed. This section may be combined with the familiarization flight above, and will continue til adequate proficiency is shown by the student.
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Wheel Landings - These landings are required by the FAA, and are the ones most tri-gear pilots tend to struggle to master. They require actions which are counter to most pilot’s training, and tend to demand a subtle hand to pull off well.
So getting to the point where a tailwheel endorsement can be given is more than just going out and flying. It is expected that most pilots who are current can make this transition in six to ten hours. But there is no set amount of time, and everyone simply takes the amount of time they need to get the sign-off.