trublesome tailwheels, ground looping
I had a 1/4 scale J-3 Cub that would ground loop if a bug walked in front of it. I have other tail dragger airplanes that you just power it up and they track beautifully with no messing around. I think I know all the rules but in my own experience it is a hit or miss luck thing. Not very scientific.
The basic tail dragger is an unstable system. The problems are that the CG is aft of the main wheel contact point and at low speeds as the tail horizontal tail unloads the wheel to the point that it is not making any side force as the tail tries to swing around. The horizontal tail seems to lift sooner that the vertical tail gives directional stability. If there is any misalignment in the main gear wheels it will show up in the ground loop.
Grass takeoffs work better sometimes as the grass gives more drag on the tail wheel holding things straight.
A tail skid instead of a freewheeling wheel will add drag aft and help.
Lots of prop thrust that can get the vertical working before the tail lifts will help.
Holding up elevator will help with down force at the tail will increase the effectiveness of the tail wheel.
I think that toe in of the main gear is supposed to help also.
I don't think that the castering tail wheel is supposed to help. I believe at least one of the fighters in WWII had a tail wheel lock for takeoff.