1. Do You think it'll make sense to get initial PPL training on a tailwheel plane somewhere else if You won't be able to fly and charter taildraggers at home after that or will have to go far to fly some? Is the quality of training so much better?
OK it doesn't 'make sense' as such, but if I had the oppotunity to go back and learn from the start again, I would have learnt on a taildragger. I'm afraid I don't know of any schools in the US that do tailwheel (I'm sure there are some though), all the ones famous in Europe; OBA, Orlando etc etc don't have tailwheels.