I think a lot of it depends on how the boat is setup. If the boat is setup properly, with single-handing in mind, then a boat in the mid-30's is probably just as easy to single-hand as your current boat. However, some things, mainly due to scale, are just going to be harder to do.
Your sails are going to be larger and heavier. Raising the mainsail, reefing it, flaking it, raising the genoa, furling the genoa are all probably going to be more difficult.
Your ground tackle is going to be larger and heavier. Stowing your anchor is going to be more difficult. Raising it and dropping it may not be, especially if your next boat has an powered windlass.
Your lines are going to be longer and thicker. Coiling and storing them is a bit more difficult. Docking is going to be a bit more difficult, since the boat will be wider, longer, and often make it harder to see where the dock is in relation to the boat. Also, the distance from the deck to the dock may be considerably different... making getting on and off, and getting the docklines tied off more difficult. Finally, the boat will have considerably more windage than your current boat—which may make docking in a cross wind far more interesting than it currently is.
The boat is going to have far more inertia... so your old habits of fending it off manually are going to have to change or you're more than likely to get badly hurt. A boat in the 25-28' range is probably under 8000 lbs. A boat in the 35-37' range may well be 12,000-20,000 lbs.
A larger boat will be less forgiving in many ways as well. If you had a problem with the roller furling, dealing with it on a larger boat is a lot more difficult. If the windlass dies, raising and lowering the anchor is going to be far more difficult, not only because the anchor is larger and heavier, but also the rode itself will probably be heavier and longer.
Beth Leonard, author of the Voyager's Handbook
, said that when they moved up to the larger boat, she was glad that she had started on the smaller boat, as the smaller boat was often far more forgiving in terms of poor seamanship. The forces on the larger boat's larger sails, and the boat's greater inertia means that it is often much harder to recover from making a mistake, as well as possibly more dangerous to make the mistake in the first place.
Yes, as the previous posts point out a larger boat tends to react less quickly...but if you make a mistake, the forces involved are generally a lot higher... A gybe with a 200 sq. ft. main is a bit different than one with a 300-350 sq. ft main.
One last point—a bigger boat will often draw more water... so some of the routes you're used to using may need to be revised.
One of my friends found this out the hard way, going from a 24' trimaran with a 4' draft (dagger board down) to a 36' monohull with a 6' draft.
Got stuck a few times in the learning process.
I'm considering moving up about 10 feet in boat size from the mid-20's to the mid-30's and I have a question.
Is it much harder or easier to single hand a larger boat, in what ways ?
I suspect it is more difficult because the sails are bigger and the boat is probably more unforgiving. I know in my mid-20's sized boat I am able to dock it pretty easily and if it starts moving in a direction I don't like I can just push it with my foot off of a piling or whatever and force it into place, I don't know if I will have as much success with a mid-30's sized boat.
What are the kinds of things I will have more trouble with on a bigger boat than on a smaller boat ?
Expenses will be higher, etc, obviously, but I mean in terms of actually sailing it, anchoring, and that type of thing. What type of strategies will I have to change with the bigger boat ?
I guess what I'm kind of asking is how much more trouble am I going to get into ?
Please don't ask for specifics of the boat (the usual first question) - I don't know yet.
Thanks for your help!