Sickbag
I'm not sure you have the right attitude here - but I am open to being proved wrong.
You state that you have had one flight in a taildragger, but did you land it? With close to 400hrs of taildragger time and a few hundreds of gliding time, the tone of your posting worries me.
Glider tugging requires a degree of handling and skill not normally found in low-time pilots, especially if the tug is a tail dragger.
Courses and differences training will take as long as it will take - it might be 2-5 hours or you might never satisfy the instructor. In my group I have one pilot who will never fly solo in certain weather conditions, and accepts that fact.