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Re: catalina 22 vs. o'day 22
I leased a Catalina 22 for a season and have sailed on the Oday 22 (I own an Oday 23, which is very similar 22). They are similar boats, both in terms of their performance and build quality. A few factors to consider:
Catalina is still in business and can support your boat with parts and advice. Oday is long gone. However, D&R Marine is still around, and Rudy at D&R was a long-time Oday employee and has taken up the torch of providing parts and advice. And there is lots of advice to be had over the interweb.
The Oday 22 came in two models. The early models had just stub keel. The later models (from I think about 1977 on) had a stub keel with a centerboard. The centerboard models sail a lot better.
If you want a newer boat, you will certainly be able to find a newer Catalina; Oday went under in the early or mid-'80's. Catalina is still making 22's.
The Catalina 22 came in several configurations, including fin keel, shoal draft wing keel, as well as the most popular swing keel models. The fin keel model sails the best in my opinion. The swing keel is by far the easiest to trailer if that is in your plans.
A word about the keels for the Catalina and the Oday: I think the stub keel/centerboard configuration of the Oday is superior to the swing keel of the Catalina. The Oday sails better, is easier to use, and is easier to maintain. All of the ballast in the Oday is encapsulated in the stub; it can't move. The centerboard is a mostly unweighted fin that is controlled with a simple line to the cockpit. Easy to move up and down with one hand, and its easy to see how far down or up the board is by looking at how much line is in the cockpit.
On the Catalina, all of the boat's ballast is in the swinging keel/centerboard. You need a mechanical assist to raise and lower it. The crank mech. on the Catalina is a pretty robust piece of equipment, but it does need maintenance, and it can break. And the only way to know how the board is positioned is to crank it up or down fully, then adjust from there. I never really liked that. And having the boat's ballast hanging by one (albeit robust) pin never sat well with me.
One more big difference: on the Catalina, the "head" is in the v-berth, which is out in the open cabin. On the Oday, it's behind an actual bulkhead with a door. When we sailed the the Catalina, my wife hated having to put the hatchboards in and close the companionway whenever anyone had to use the head. Very inconvenient, and especially hard on day sail guests not used to the experience. I had one guest tell me years later that she held it all day rather than "make a fuss". Never underestimate the value of a private head when sailing with the ladies or guests.
That all being said, I would buy the boat that was in the best condition: a sound deck and hull, good sails and working outboard are the primary considerations when buying a boat this size. Fixing or replacing any of those major components will come close to exceed the value of the whole boat. Good luck.