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!?!
Reflective Hull Decals
Bent Shaft Canoe Paddles