re: First boat: Cal 2-27, Pearson 28 or Islander 28?
I bought a Cal 2-27 back in March of this year. Though I learned to sail years ago, this is the first boat I've ever owned, skippered, and single-handed. Mine cost just a little more than the one you looked at, but it had a working Atomic 4.
We've really enjoyed this boat. It's simple, apparently bullet proof, and pretty nice in the interior compared to other boats I've seen in the same class. I love all the wood. I've told many people, "it's the perfect boat for us" (family of four, mostly new to sailing, not a lot of extra cash to throw around, etc.) It's a nice size for doing some overnighters while not being impossible to get in and out of our tight slip. That said, I would not be overly enthusiastic about getting one with an outboard. My own personal preference is to have an inboard, and not having one would be a show stopper for me (unless repairing the inboard worked out in the total dollars.)
As far as changing the name of a boat, my feeling would be to pick a new name, paint it on the transom, and do a dance on the fo'c'sle daring Neptune to do anything about it since it's your own damn boat and not his.