Do you actually have the "system"? Hammock, straps, tarp, quilts? Fine if you do, go use it. Get a feel for it as ENO is not bad stuff, its just not directly targeted to the backpacker, but more the camping enthusiast. Not that you can't backpack with it, but as you probably know, the fat biners need to go!! Get some mild weather camping in while you can, THEN start watching Shug's winter videos - not only is it all good info in an entertaining format, but you're left with the impression that if this clown can do it then certainly I can.
p.s. THEN you'll know what you want for winter time. Winter is a steeper learning curve for the hammock part, but sounds like you're an old hand at the "being in the cold" part.
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