re: First boat: Cal 2-27, Pearson 28 or Islander 28?
I can't give you direct feedback on that particular Pearson, but have sailed in smaller and larger models. What I can tell you is the Pearson has a very good reputation for solid, well-build, well-designed boats. They used quality materials throughout. Personally - I am biased :-) - I would have thought the Pearson is likely to be the best built of the three.
As always, it comes down to condition and price. All three are quality boats, but if you intend to sail in The Slot (I think you mentioned SF), then I would err on the side of a strong, well-built, seakindly boat. it can get rough and windy out there.
BTW, don't worry about changing the name. Just follow an "official" de-naming ceremony, and don't stint on the champagne. An awful name is worse luck than a rename.....