Sooner or Later (a boat)???
I think that one point that you may be understating is for most, if not all people, learning on a small boat will make them way better sailors and accellerate the learning curve, and one thing that you are over stating is the importance of learning the sailing ground that you will ultimately sail on. I have sailed the Chesapeake for 20 years and I am still learning the sailing ground that I sail on. That is a big part of the fun of sailing.