re: First boat: Cal 2-27, Pearson 28 or Islander 28?
I learned to sail on a pearson 28. Although I love my Ericson I always remember how kind that person was to my less than salty maneuvering. All these boats are great, but I can say from experience that the Pearson is a great boat, and great for the novice sailor. In fact I know a ASA instructor who looked for that boat to teach his 101 classes on because its so forgiving to the unexperienced, while performing well for a more mature sailor. Plus the cabin has some serious headroom for us 6'2" boaters.
Cheers, and remember you'll fall in love with it no matter what your first boat is, and thats the real tick anyways.
1976 Ericson 27'