Thanks for the update. It's a common theme for people to ask about what boat to build, but it's rare that we get such great feedback later. I'm about to build a gunter-sloop Take Apart Passagemaker, so this kind of info is valuable to me.
I ended up building the PMD with the sloop rig. I'm quite pleased with the boat and its performance.
I have three key points I didn't expect/believe before i started using my boat.
1. I really need to make sure everything is rigged and tensioned correctly at shore before I start the trip. It's a real pain to climb up to the bow (potentially over people) on such a small boat to attempt to adjust the tension on something or re-tie a knot once we're out on the water.
2. Space/comfort of passengers. When I'm out on a large lake where I can sail in one direction for an hour+ I can put 3 adults or an adult and 3 kids on the boat relatively comfortably. There's a surprising amount of space to stretch out and rearrange without putting the boat off balance. On a small lake with a lot of tacking/jibing it' pretty much shrinks to 2 people, or it's a very short trip because they get tired of having to duck under sails/lines and shift around and/or rearrange every few minutes.
To be fair, I expected this... it's a 100 pound boat that's less than 12' in length. There's only so much space and seating position is important as people are the balast. I live in central WI and sailing isn't really a big thing in much of the state, so my passengers tend not to expect/understand that. Setting expectations is important.
3. Realistically this boat isn't car-topable. I did it for the first part of the summer, but it's a real hassle and it means all of the gear goes inside the car... mast, boom, anchor, oars, etc. Just expect to need a trailer. Most of the equipment can be packed into the boat if it's on a trailer, and I can pull it with my sedan rather than having to take the family car without room for any of the family.