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Getting that winged keel stuck in the mud could create a lovely piece of sculputre on a pedestal for passers-by to enjoy. While the big Irwin may look fast, it probably isn't. At 165PHRF, the smaller one isn't either. A shoal-draft C&C 33 Mark I rates 153, and that's for a shorter boat! We have a friend who singlehands his T37 Wednesday nights and manages quite well in the non-spinnaker division. A Tartan of that vintage probably has had time to develop just about all the issues it might, and have had them fixed. (You say major updates.) I'd suggest getting Practical Sailor's Used Boat Buyer's Guide and giving it a thorough read.
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