She does that a lot.
Negotiate with the club to store her there over this winter, then sail her down in the spring.
I'm confused, then, why you think you'll be game for gutting the other boat while she's in the water. That's going to be a physically demanding job, probably moreso than motor-sailing that 27 from Philly to the Chesapeake.
I'm in my 40's, so maybe I don't have the right perspective. A 25' and 27' boat are going to have close to the same sail area, so the force on the sail is going to be approximately the same. That means that the strength you'll need to wrestle the 27's sails will be about the same as a 25. If the issue is with the ability to control a 27' when you're used to something smaller, I wouldn't worry too much. We jumped from a 14' rental to a 25'. It took about 3 tries docking to start to get comfortable. The next year (this past season) we jumped to a 31. I think the "new" boat is easier to handle than the 25.
negotiating is an idea. I will have to consider that. I didn't mean more than I can handle as far as size. from my experience, it's actually easier sailing a bigger boat. less tender, etc. my 9' dinghy is the most challenging boat I have sailed, once the wind gets up, even if it was my first boat. when I bought the holiday, I will admit I saw the size and was a tad nervous about it, but it's a lot easier to sail than my dinghy. the first time i took her out, I single handed her. hell, she even sailed herself, one time, while I was up on the bow lashing down the jib, after lowering it due to suddenly high winds. that's a funny story, too. never tell a person who hasn't sailed," hold her steady as she goes", as you get up and walk to the bow of a boat. you really need to make sure they understand they have to hold the tiller, first.
I meant that I am thinking a boat nearly 30 feet would cost more to maintain and store. when calling marinas, they all asked the size of the boat before giving me a price. but, I do see what you mean. 24' to 27' is only 3'. lol.