They have a cool factor that entices and can utterly disable the ability to make a rational purchase decision. More than a few pilots you hang with claim that you’re not a real pilot until you fly tailwheel. Plus, watching one slip down final to a deliciously soft touchdown on a grass runway just plain looks like more fun than is legal in many states. What’s involved with learning to fly a tailwheel machine? Can you rent one once you do so? What’s a good one to buy? Can you get insurance if you decide to buy one?
The quick answers are that the FARs require specific training and an instructor’s endorsement to fly a tailwheel airplane as PIC, some operators that give tailwheel checkouts do rent the airplanes to you once you’ve completed it and the current insurance market means that you will probably have to jump over some manageable hurdles to insure a tailwheel bird if you are under age 60—the hurdles get successively higher once past 60. We’ll go into depth on all of that and more below.