Playing on a grass.
As I was signing up, the person at the counter asked me whether I wanted to learn in the high wing or low wing and, in case of high wing, 152 or 172. Seeing the blank expression on my face, she gave up asking and just put me down for a Cessna saying I could always switch to a Piper later. One glance inside one of the numerous 152s on the field convinced me that I wanted a "bigger Cessna". That's how I ended up learning in a 172M.
By the time I finished my PPL and signed up for the tail wheel training, I was feeling reasonably confident in my ability to fly and (more importantly) land a 172. My PPL instructor liked taking me up in gusty x-winds, so I thought I got my x-wind inputs down solid. I have also been exposed to shorter and grass strips and was comfortable with those as well.
Takeoff directly into the wind was relatively short as the plane did not really get any chances to do something bad. Once in the air, that plane turned from an uncontrolled wild creature into a precise flying machine. At least it was precise when I remembered my rudders. It let me know instantly when I did not – such a chance from Cessna!
Landings were relatively easy ( and I am pretty sure that having an instructor in the back seat that did not want to crash that day helped too). The easiest part of the PPL training for me was always arriving at the numbers at a precise speed – I can’t do the math or what I need to add or deduct in terms of pitch and power, but I somehow intuitively know when to make these corrections. Citabria was the same once I adjusted to the sight picture (it flies much more nose down compared to Cessna) and required speeds.