Welcome aboard Westfield,
Well, I read your post to my wife - she said, "They started at the wrong end of the scale!" :wink: Very few people would have a problem on a 59' luxo boat. Moving down in size to a 25 or 27 foot boat takes some MAJOR rethinking of priorities. With our smaller boats, it isn't what you don't have, it's what you can do. I can stand up or sit down in the shower in our head... go without a shower for a few days, and she'd be delighted to sit down and shower! OK, that was tongue-in-cheek - hope she has a sense of humor. :wink You already know about the trailering aspect. In the first year and a half of owning our 25, we went from coast to coast to coast with the boat. Winter in the Florida Keys or the Tropical Tip of Texas and summer in the PNW. Along the way, we went to great places like Lake Powell, Flaming Gorge, San Francisco Bay, Yellowstone, Lake Tahoe, etc. We have spent up to 5 months at a time onboard our CD-25.
If you look at it as "stepping down", you will not likely be satisfied with the experience. If you see it as the opportunity to see quiet coves that deeper draft boats can't get into, get under bridges that taller boats can't pass, and be able to experience different waters easily thanks to the trailer... well, it opens a lot of new horizons.
Having said that, it isn't for everyone. If you aren't both onboard with the idea, take a pass. Save yourself the frustration of trying convince her that she's having fun. But if you have that couple hundred thousand budget, you can always get one of these boats for travel AND get a midsize trawler to keep in the water nearby.
Wefings, in Florida, is a dealer who has a 25 Cruiser available for charter. You can try before you buy. It's not the Inside Passage, but it is beautiful turquiose water, white sand beaches, and warmth. She may not want to go back north. :wink:
Now, none of this is exactly on-topic regarding your question about the stability and trailerability of the 27 foot boats. We've towed longer sailboats with no problem. In my personal opinion, beyond 30 feet, a trailerable boat, travel trailer, cargo trailer, etc. becomes a lot of work on the road. The stability on the water depends on the design, hull shape, and water conditions.
If you want to see how some of us are using these boats, check out Bill and El's Halcyon Days website (link on the lower left of the home page here) or the Grand Adventures forum.
Good luck convincing the Mrs. If she gets it, you may find a world of wonderful experiences out there. Keep us posted.
Best wishes,
Jim B.