re: First boat: Cal 2-27, Pearson 28 or Islander 28?
Sometimes I think I'd feel safer in a small dinghy. At least it won`t go anywhere if I fall overboard.
For pure sailing, a smaller boat is so much nicer... sigh. There is nothing like the sensation of being part of the boat, one arm feeling the wind through the sheet and the another one feeling the flow of the water on the tiller.
Dinghy sailing skills are completely transferable in the sense that you will know when you are doing something stupid even if your large boat does not immediately sends the feedback. Now, knowing how to right a boat should hopefully be less useful.