Join Date: Aug 2010
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I just bought an Allied Luders 33. I think that could be a great boat for you, especially if you are already familiar with it. I love ours, and feel good about singlehanding it. I have a partner in the boat, and I can say for sure that that made a huge difference when we hauled the boat. Two people flushing the systems, cleaning up, and covering it and worrying about it worked well and made me more comfortable that I had all my bases covered. Also expensive repairs get 50% cheaper.
The Luders is pokey, but easy to handle, rock solid and they can be surprisingly affordable. In fact, you should look at the all the Allied boats, which tend to run on the cheaper side of things but are still very able. I see Seawinds for under $30k (I don't know much about them).
My partner, who is saltier than I, says, the key to a good partnership is not sailing with your partner. We divide up the time and when it's your turn with the boat, you own the boat.
Also if you think you will be singlehanding a lot, get a good auto pilot. I use that much more than I thought I would, even with crew aboard. But it's great for running up and setting the sails or untangling a situation if there's a problem. Good luck.