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AferLazzo,
I have a friend with a T27, and he sails the heck out of her. I know that she is not a racer, but if you will be single-handed cruising, I would feel safer in the Tartan than the Catalina. Of course, the Tartan 27 is getting quite old now and she would have to checked over carefully before buying. The Catalina may have an edge on performance and you can certainly find a newer model than the Tartan. You got it right when you said that these are two totally different boats!!! I would honestly analyze what type of sailing you are planning and proceed from there. The Catalina is really for bay/near shore sailing with her fin keel and spade rudder, but she is roomy down below. The Tartan is able to go further afield with her full keel and will be more sea kindly and have an easy motion. Either boat will need upgrading for off shore work.
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