re: First boat: Cal 2-27, Pearson 28 or Islander 28?
You might reconsider. Why buy a boat without a working engine in this market?
I know others will disagree, but I am concerned about seeing a boat designed to have an inboard, carrying an outboard engine added to the transom. It looks like someone cut corners and was too cheap to repair the inboard.
If I were you, I would not get too attached to any particular boat. Just look for the best deal in your price range.