It depends on who the single hander is. If we have been a while off the boat every line on mine and a few from other boats ends up wrapped around my ankles. When I single my techniques to maintain boat speed while trimming the sails correctly are less than smooth. I would say that most of the sailors who race regularly have attained a level of proficiency where they could be considered "even" skill wise. They may however, get beat regularly and maybe by a lot because of what Pepin described. Simple smooth boat handling can easily be a boat length or 2 in each tack and 4-5 boat lengths around a mark. (Course 2, 6 legs, 6 roundings, ave 3 tacks/jibes per leg = easily 50 boat lengths) Most teams are not losing by nearly that much.

Boat only handicaps can not include every parameter like self tacker, winged masts etc because if they do, their gain or value is really dependant on the crew making them work. Adjustable things can make you quite a bit slower in reality just because you end up adjusting in stead of sailing.

Maybe we need a handicap scoring system based on teams; people and boat together. We used to use this in our old fleet in the midwest. Most of the guys were on H16 but it worked fine for the random 17, 20 or 18 who also raced. This way you have a personal handicap score that is tracked just like bowling or golf. You do well in an event and your rating drops. Unfortunately there are but a few of us racing these days, so compiling a start place would not be that difficult technically. Getting agreement as to any particular number for some individuals will be.