RE: when do you know you are ready to go to third plane?
A possible answer is to ask to fly someone else's plane that is similar. It know it sounds far fetched, but many folks in clubs will sometimes allow newer pilots to fly a faster or more aerobatic plane to see how the new pilot can handle it. I'm not saying take-off and landings, but up in the air (three mistakes high!) I have been on that route, and it really opened my eyes and those that have flown my planes. The Shoestring can be a handfull. They like to fly fast and can be a pain to land if you are used to a floater. Or, have someone with more experience in your club fly it for you and let you get some stick time on it. My 2 cents