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To start with, while many of my ideas match many of the latest throughts on short and single-handers, I know that my take on what makes the ideal single-hander is a bit different than much of the conventional wisdom and I also believe that this is another topic where there isn't one universally right answer. My point of view has evolved over the 45 years that I have been single-handing boats, and while I have owned and single-handed boats that conventional wisdom would call nearly ideal, I know that I have evolved my own own ideas through trial and error and so admit that they may only represent one person's opinion, mine.
If you really expect to do a lot of single-handing then there are a variety of factors that can help make the boat easier to handle. As has been suggested it does make it much easier to single-hand a boat if the halyards, vang, and reef lines are lead back to the cockpit. It is very helpful if the mainsheet, traveller, backstay adjuster, and jib sheet winches are within easy reach of of the helm. I suggest that lighter weight boats with higher ballast ratios and easily driven hulls can get by with less sail area, in my opinion making them more ideal as single-handers.
The whole thing about single-handing is that the boat needs to be set up to do things reliably since you do not have extra crew to assist if something goes wrong. On that basis, I strongly believe that in-mast furling hs no place on a single-hander. Similarly, I strongly recommend a two line reefing system that can be left rigged for each reef point. Also similarly, I strongly believe that fractional rigs proportioned for minimally overlapping headsails makes an ideal rig for single-handing as they are easier to tack reliably and require fewer sail changes. I suggest that mid-boom sheeting and cabin top mounted travellers are less than ideal because of the high frictional losses and lack of convenience from the helm.
A reliable auto-pilot is extremely helpful, especially if you plan to fly spinnakers. Windvanes are great if you plan to make longer passages. On smaller boats (under 36-38 feet), tillers with tiller extensions can make it easier to single-hand because you are able to move around the cockpit and still steer.
While Tartan and Sabre build nice coastal cruisers, from my perspective most of the rig design, and deck layouts on their 32 to 36 footers make them pretty poor single-handers.
Respectfully,
Jeff
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