big boat, 50' with 40,000+ displacement. 450 sq. foot main.
We have 2 deep reefs. We use the first reef quite a bit as the boat seems to like that first reef in more than 15 knots true which is pretty much standard wind speed in the trades. With the first reef and 17 knots over the deck ahead of the beam the rudder is centered. At that time I adjust or reef the headsail until she feels right and the crew is comfortable.
When the wind picks up to 28 to 30 or more I put in the second reef. Along with the second reef the headsail gets rolled up with usually about 10 or 12 feet of foot out. With the second reef and a handkerchief of a headsail out (30 knots +) we do about 8.5 knots and the boat is happy, upright and the rudder has just a very small bit of weather helm (that's good). If I try to go faster which we can easily do it just stresses the boat and tires the crew. Not worth 1 knot of additional speed.