I hear there is a pretty nice article about paddling the islands in this month's Sea Kayaker Magazine :-)
There's nothing currently being orgnaized like an island race in the Erie Islands area. For someone to take on this endeavor, there are a lot of logistics similar to a road race, including but not limited to weather, paddler ability/safety, taking registrations, and liability. The Keelhaulers can for sure advise on the difficulties in planning a race and theirs is point A to point B, on a river. Doing something in open water adds layers of complexity. It can be done, but libility and safety is a huge talking point.
My guess is that the original poster was thinking low hassle/his schedule on the initial concept, but didn't elude to how the money was being raised? Don't ya love ideas from the peanut gallery!?!
Paddler's Truck Rack