Well, I've just sent an ATPL jet pilot solo in his new (to him) flying boat taildragger, after about 4 hours of dual. Aside from the tailwheel course I sent him on last year as a prerequisite, he had not flown GA for 15 years apparently. After hour two, backtracking the paved, 100 foot wide runway, I drew his attention to the "S" path black rubber skid marks crossing back and forth the centerline - and told him that he'd just made those, and the other ones we were about to get to as well....
For the four hours, I never touched the brakes on the right side, though I did floor the right pedal a few times. We kept it on the runway.... He knows the electronic stuff really well, and brought his Ipad along to navigate the circuit. I put it in the seat pocket, 'cause we did not need it to navigate. Then I promptly broke it, by leaning back in the seat against something behind. We still found our way around the circuit okay, and he got enough skill to go solo - without the Ipad.
So now he practices solo, and soon we're headed for the water part of the training.... (This Ipad will stay ashore).
But I'm proud of him, he took on an unfamiliar challenge, and is mastering it - the old fashioned way!