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re: First boat: Cal 2-27, Pearson 28 or Islander 28?
Also, is there a big advantage to a x-long (25") shaft? I've been considering a new 6hp Tohatsu sailpro, which is only $1500. The main attraction is the long shaft, so I'd appreciate any opinions on that.
You will need a 25" long shaft to have an outboard even have a chance of working well on a 28' boat.
A 10hp (or maybe slightly larger) motor is what would normally be recommended for a boat of this displacement.
4-stroke motors are quieter, cleaner, more efficient, and don't require blending oil into the fuel.
Our Catalina 25 (over 2000lbs lighter than the Cal 2-27) had a Tohatsu/Nissan 9.8hp 4 stroke 25" shaft motor. It normally ran at the lower end of the throttle, but the higher power was occasionally useful when fighting big headwinds.