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If your primary concern is ability to sail to windward, then I would say the Catalina 25 would be the first choice. I owned a fin keel C25 and raced it for many years, and the swing keel C25 is reportedly faster than the fin by a miniscule amount. I have no experience with an Oday 25 CB, but raced against a fin keel Oday 25, and it pointed and footed nicely, so I would guess the Oday would rank at least a close 2nd in pointing. The CD would rank 3rd in pointing.

But, you should choose the boat that makes all the best compromises for your particular use. If you are planning to do mostly fair weather coastal cruising, the C25 will work well. None of those boats should be in sustained heavy weather, but the CD would be the better choice if prolonged heavy weather is likely.

And, my first concern in buying a boat is to find one that is fundamentally sound and in good repair. You know, better than us, how you intend to use it, so you have to make the compromises that will fit into your plans for the boat.
 
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