FWIW, I enjoy singlehanding my boat but pick my days. The sails are not the biggest challenge. For me, it's always been docking. Docking can be challenging in a crosswind or in strong current, and I learn something everytime I go out. The bow of a sailboat wants to spin downwind as soon as she loses forward way. This year I started "backing in" when the wind is up, and that proved a better alternative. The bow follows the keel that way. Before docking, I rig my fenders and have lines bow, stern, and spring, coiled at the gate, ready to take myself onto the float, or hand to someone else. The tricky part is stopping the boat alongside the float and getting from behind the wheel thru the gate onto the float with docklines in hand, and secure them before the boat reacts to wind and current and the bow spins. I think I've learned a lot docking the boat for ten years, and the only scrapes occurred from dockside helpers who tend to pull the bow line in too tight. I feel docking is still the most challenging aspect of singlehanding. The more you know your boat and the more practice you get, the better you get at timing your turns and controlling your approach speed, and the easier it gets.
Having the jib on a furler is a must and some days you can sail with just the jib and not have to deal with the mainsail cover or flaking the sail. I use an autohelm to steer the boat and raise the mainsail by hand, using the winch only for the last few inches. When I bought my boat there were two frozen sheaves for the main halyard that forced us to use the winch. I didn't find the problem until the following summer and then I freed the sheave at the mast deck collar and the sheave in the deck organizer and lubed the track and now anyone can raise the sail without the winch. I plan to install lazy jacks, but meanwhile I have to wrestle the big sail onto the boom and reflake it at the dock, before putting on the cover. Occassionally I have my son along and one lowers the halyard in a controlled way so the other can flake and tie the sail on, but lazy jacks would make the job a little easier. Summary: you'll get used to the bigger boat so buy the biggest you can afford, don't forget the annual costs of slip fees, winter storage, insurance. Research and know the value of things. One new sail costs more than a whole instrument package, or a good feathering prop. Setups for singlehanding should include good roller furling, lines led to cockpit, a reliable engine and good engine controls (remember docking), lazy jacks. If you're handy, things can also be added to an otherwise good boat. I added the Harken furler and autohelm and many cruising amenities to my barebones racer, but your boat should include those things. A professional survey will run around $600, so presurvey a few boats yourself before going to that step so you only have to pay that fee on one boat. Happy hunting. Chuck Resolute 1990 C&C 34R Atlantic City, NJ
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