The thing is if the weather is bad it's not worth going. We went on a river trip in Late October and it was high 60's and got down into the 30's at night. It was doable but anything lower and/or rain would cancel things. Weather wise early May we shouldn't have to worry about temperature but the rain could mess things up.
My buddy has 6 canoes and I have a Kayak (1 person). The thing is he doesn't really like other using them unless he is around. If we had SUV's you can tie 2 canoes on top but a trailer is definitely easier (my buddy has a canoe trailer as well).
Commitment wise will depend on the date. I have graduation the first week-end in May so the second week-end would definitely workout better for me.
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