I’m a recently-minted private pilot with about 70 hours, and a little over 3 hours into tailwheel endorsement training. Interestingly enough, the tailwheel endorsement has been my big goal, perhaps even more so than the PPL! But there is an order to things, and these days the PPL checkride is mostly tailored to the Cessna 172. There are exceptions, but this seems to be the general rule.
Thus, I worked through my private pilot training mostly in a 172 (with some 152 time thrown in for good measure). Meanwhile, I read just about everything that I could get my hands on related to mastery of a tailwheel aircraft. There are numerous online resources, most of which are very good. There are books, including the bible of tailwheel flying, Wolfgang Langewiesche’s Stick and Rudder. I own it, and read it cover to cover.
The analysis of tailwheel aircraft physics and techniques contained within these tomes is wonderful, thorough information. However, after enough reading of the materials I realized that I had actually developed an apprehension about mastering the complexity of the system. Anxiety had crept in, and I wondered whether it was even worth the effort to learn the management of a seemingly fickle and obsolete design.
Enter actual tailwheel flying. I took and passed my private pilot checkride, and the very next week began tailwheel transition training. With no offense intended toward all of the excellent writing on the subject, the actual operation of a tailwheel plane is simple: keep the small wheel between the two mains. Or, put differently, keep the nose pointed straight. It requires coordination of the rudders and the ailerons, but reading about it won’t grant you mastery of it. You have to develop muscle memory and instincts to keep the plane pointed in the right direction, and this is done by actually spending time in the plane. Despite the complex physics involved, I haven’t found it to be complex at all. It simply requires more care than a nosewheel plane.
In my limited experience, I have noticed that pilots have different interests. Some pilots, many in fact, gravitate toward technology. Glass panels, carbon fiber, and “slippery” airframes are the name of the game. My interests seem to be regressive. I am getting the most fun I have had flying out of a drafty, wooden spar, fabric-covered taildragger, with a modicum of antiquated steam instruments. Most tandem-seated taildraggers, like the one I fly, are designs of a bygone era, with the glide envelope of an anvil and enough adverse yaw to mandate authoritative rudder inputs… if you don’t intend to fly in a straight line until out of gas.
If you’re a regressive pilot like me, who really wants to have the experience of aviating (and not merely piloting), I would encourage you to pursue the tailwheel endorsement. Find a good instructor, like the one I have, and start spending time in the air. By all means read the books as well, but remember that there is no substitute for the real thing. I think you will find, like I have, that tailwheel flying is actually one of the simplest, purest forms of the craft.