Taildraggers demand a higher degree of skill from their pilots; due to their configuration, they are more likely to groundloop if improperly handled, and can be difficult to taxi, takeoff, and land in strong winds.

Why, then, do people fly these airplanes? Many reasons. Tailwheel aircraft have a dramatic advantage when operating from short or rough fields; a survey of bush planes in Alaska, Africa, South America, or elsewhere will reveal a hugely disproportionate number of tailwheel aircraft. The tailwheel is far less likely to get stuck in the mud and grass, reducing the chance of a nose-over or collapsed nosegear.

Bush flying isn't the only reason to fly taildraggers, though. For the first half of the aviation age, all airplanes had conventional gear (hence the name “conventional”). Many of these airplanes are still flying, and stir the hearts and souls of pilots who see them. Who wouldn't enjoy playing with a Stearman on a beautiful summer's day, or cruising low over the Earth in a Piper Cub with the doors open at sunset?

Most aerobatic airplanes are taildraggers, too. Citabrias, Pitts, Extras—all taildraggers. If you want to get into aerobatics, odds are you'll have to learn to fly a tailwheel.

Even if you have no interest in flying tailwheel aircraft, though, a tailwheel endorsement is a great way to improve your flying and enhance your skills. Taildraggers are less forgiving of side loads and improper wind correction during landing; with tailwheel training, you'll quickly learn to align with the runway perfectly, every time.