mrsnow-
Hello! This is going to sound like heresy around this C-Dory site, but here goes!
The Skagit Orca 27 is a bigger, better built, and even more seaworthy boat than the C-Dory 25.
It has much more standard equipment, has much better fit and finish, and is more of a deeper V hull than a C-Dory 25. The deeper hull will ride better in choppy conditions.
It also is an inboard, usually having a large Mercruiser single big-block V-8, the associated I/O drive, and will consequently use more fuel than a C-D 25, probably quite a bit more at that! The boat needs the big V-8 because of it's size and weight, although two big outboards of 150-200 hp could have been used.
The cockpit will be higher due to the inboard housed below, and there will be some step ups and downs with the cabin and cockpit being at different elevations. (As one gets older, the up/down routine gets harder to accommodate!)
I looked at several of the used ones for sale on the East Coast before I started to write this, and I'm glad a couple of them aren't here closer to where I live, or I'd be tempted to trade up today! (Priced no more than a CD-25 would be out here on the West Coast.)
Looks like you'll have to buy a trailer if you plan to trail the boat, but around $5-7k should get you a nice new one back there.
I don't know if fishing is on your agenda or not, but if it is, be sure to figure out if the cockpit floor level is so high that you'd be a lot better off with a cockpit floor much further down in the boat with the engine surrounded by a housing.
Overall, the Skagit-Orca 27 really looks like more of a high quality cruiser than a fishing boat, for sure. (I've seen them at boat shows before.)
Sounds like a good fit between hull and your ocean and ICW conditions back there, too!
Biggest disadvantage to me would be the I/O drive, since they need to be serviced every year or two, depending on use and storage conditions, and can be problematic because of their relatively complex design.
Will you be keeping the boat in the salt water? (I'd prefer to keep it out of the water, so the salt doesn't eat at the I/O unit.)
If you decide to go ahead with a purchase, be sure to have the boat surveyed throughly and plan on going through the I/O unless you're sure it's been done very recently!
Have you looked at the Skagit-Orca 27 yet? It will seem like its at lease twice the size and weight of your previous CD-22, and the upscale appointments compared to the spartan C-Dory will be apparent!
Others will add their two cents, but this is mine off the top of my head at 5 am on a Saturday morning!
Good Luck, whatever you decide!
Joe. :teeth :thup