Hi Ajax! Haven't been here in a while but found this interesting.
What others havce said makes sense. When we doublehanded Rita P, it was two wraps on the winch, get it in most of the way, then one or two more wraps to get that last bit in. A lot of the time I ground myself while stickboy steered, but in conditions like you had last night, stickboy would steer with one hand, tail with the other to help me out.
You don't want self tailers on a race boat. But I sure do like 'em on a cruising boat!