The Compleat Taildragger by H.S. Plourde was the book I used to study the subject, it should be available used though it is out of print. It takes several chapters to explain everything, but you can get the picture in a few hours if you get the book.

Tailwheel takes more skill than tricycle to land successfully, and it is good training to learn them. They are the ideal aircraft for shortfield operations, and they are cheaper to build and maintain. I had a very shaky grasp of stick and rudder flying until I learned how to fly the J3 Cub. I have never ground looped but apparently it's not too bad if you don't scrape a wing or twist your neck. A greater and more damaging risk is actually that of running off the runway into a ditch since you have so little steering authority.

Tailwheel was the preferred design for piston fighter aircraft in WWII so the props could be large, and they are the best choice for short field and grassfield operations because they turn on a dime at the end of the runway, they have no nosewheel to drag in the mud, and they make it easy to keep your prop out of the dirt. I do not know of any purely aerodynamic reasons they are preferred for shortfield and grassfield, to me they fly a lot like similar tricycles.

Many people do not know that you can land a Skyhawk-type tricycle airplane like a Cub. Before the time of paved runways this was how people had to land them on the grass, and Skyhawks in particular had a 40 degree flap setting to facilitate fence hopping and ultra shortfield uses.

When you consider the simple construction of the tailwheel airplane they make the most sense in a rough environment due to the tougher tubular construction. Of course, later tailwheels usually had monocoque construction but the Supercub was tubular until the very end. And of course they have an aura of mystique as they are the airplane of such a vast portion of modern history.