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My advice would be to look at the equipment. They are both great boats, and the layout to you seems like not too big a deal to you - so think of the boats as a collection of parts. What are the upgrades you would need to add to the Cal to bring it up to the level you would like - both in terms of cost and time. Now do the same calculation for the Pearson. Consider the big ones (standing rigging, engine, sail wardrobe) and medium (pressure system, water heater, autopilot, overall electronics age/condition). If you are like many of us, buying, mooring and maintaining the boat uses up a lot of funds, leaving not much else for upgrades...so sometimes a well-equipped shabby will be a better decision than a well-maintained spartan....
 
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