re: First boat: Cal 2-27, Pearson 28 or Islander 28?
I cannot comment of the Pearson although they were reportedly good yachts. I have sailed on both the Cal 2-27 and the Islander 28. The Islander was a somewhat more costly yacht at the outset than the Cal with quite nice finishes and more elaborate detailing. That said, however, the Cal was quite well built and in similar conditions, sailing out of Sausalito, Ca., we found the Cal a somewhat better sailor. Both yachts performed well however, so I think it is more a question of how well the boats were maintained and are equipped. (For what it's worth, we purchased and sailed a Cal 2-29, the big sister of the 2-27 for 20+ years. Great boats.)
"It is not so much for its beauty that the sea makes a claim upon men's hearts, as for that subtle something, that quality of air, that emanation from the waves, that so wonderfully renews a weary spirit."