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Hi Adam,
I am currently in the same boat as you and have narrowed my search down to a Catalina 25 or 27 which would be perfect for my purpose which is mostly cruising the coast, Bahamas and spending the weekend on the boat with my family. Eventually I want to take another couple with their kid as well. So that would be 4 adults and two 4 year old kids. Checked on Catalina 27 and it would fit perfectly. BTW, my wife and myself are 6'.
Both can be trailered as well but I think your budget might be a little bit tight for it. Saw some good ones for around 7-8K.
Mario
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