We have been doing the same trying to figure out the best configuration and potential tow system for CT. I guess we'll have 100mi on the water to get squared away!
Holy smokes. That just makes me want to cry. Let me know what you guys figure out.
Boat tows are tough! The best systems I've seen are inflexible so they effectively make the two boats into one. At Untamed New England one year, each team was given a canoe and a really crappy plastic kayak. The eventual winners put all 4 paddlers in the canoe with a homemade seating system and they just towed the kayak!