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re: First boat: Cal 2-27, Pearson 28 or Islander 28?
Although I have always liked the Cal, a re-power alone may end up costing more than a whole boat with a working motor. The cost to the prior owner to re-power my boat was twice the asking price of the boat you are looking at. My boat is about the same size and age and came originally with a A4 or Ferrymann diesel. For comparison here is one in my area that has been on the marked for a while, with a working diesel,
[link removed] Cal 2-27 Sailboat,
If you go with the outboard you will come out ahead for a time, but if the long term plan is to work out some type of inboard power you might be in for a pretty big total investment compared to a ready to go boat. That may not be a bad thing if you have the $, love the boat, and have the time and skill to get it done.
I actually looked at that boat a while ago, but I figured it would be too much hassle to get it transported to SF. Now that I've looked into parts availability for Farymanns, I'm not so sure it's such a good deal.
I realize it'll cost a sizable chunk of money to convert to electric, but I figured it'll be a fun project and would cost a lot less if I do some of the non-specialized work myself and use components or kits, rather than turn-key systems. I'm estimating around $5K to do the conversion over the next year or two, which would still be about half the cost of a diesel repower. Add to that a pair of good ST winches, and the dollars start to make a lot more sense. The outboard would be just the means to still be sailing in good weather while I'm doing all that.