As a fellow native of Oshawa, welcome to the forums. The only way to know if your solution is going to work it to test is a spot where you can easily bail. If you have can do that today (Jan 3, 2012) the weather is such that you will get a pretty good idea of your 2 bag solution with no underquilt is going to be feasible. I would at minimum use a CCF pad or a thermarest type pad to provide some insulation on the bottom side.
A group of Ontario/Eastern Great Lake hangers is heading out to Valens conservation area this Saturday for an overnighter. Details can be found here, I know it is short notice, but it will be the best opportunity for you to check out a bunch of hammock gear and speak with people that have cold weather hanging experience.
Cheers
Brian
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