I've also used an Outleader kite as you all know. After many, many outing with it, I decided not to use it on the SHTP because it was just so labor intensive. The things are wicked fast when the wind gets up over about 12 knots, but they are a lot of work. in a three-up distance race where one guy is resting while two guys are on deck, I think it'd be do-able. Anyway, I still have mine and will be using it whenever I get the next "big" boat.
I have to say that a smaller, say a J-24 sized (400 sq ft) Outleader would be really easy to deploy on a 27 - 30 foot boat. It'd make a great get-home rig. However, while they are more powerful than a standard-sized spinnaker once the wind is up, there are limits and a half-sized kite isn't gonna give you the oomph of a full-sized one.
I've had in mind to build a 16-foot traditional-looking beach-cruise sailor for a while, and I'm seriously tempted to put one of these on the boat just for yucks.
http://www.funwithwind.com/store/vie...4432&idparent=
1968 Selmer Series 9 B-flat and A clarinets
1962 Buesher "Aristocrat" tenor saxophone
Piper One Design 24, Hull #35; "Alpha"