Hi Chad, you will want to pick up Todd Bradshaw's book Canoe Rig. It's got study drawings for all kinds of sail configurations plus some general guidelines, etc. Also different types of leeboards, centerboards, daggerboards, retractable (fan-shaped) keels... I thought it would be fun to do a fan keel out of composites.

The daggerboard would need to be directly under the sail's center of effort. And, on a reach, the daggerboard will make the boat want to go forward instead of sideways. There are no hard/fast rules for sail area but, as I recall, the book has some guidelines. I have the book but I haven't tried any of it yet. I would like to maybe have a little spinnaker for moving downwind but the idea of hiking out onto the coaming doesn't really appeal to me

I hope this was helpful.
Chip
www.ChipSandresky.com