Good post, Dave - made this thread a sticky.
Brandon - I see the benefit of what you're talking about, but what if you just made the section next to the hammock from sil and all the rest from DWR? Then just use a Garlington Taco when you need it. For very little extra weight, you get the flexibility of a half-quilt, or use the taco only, and get an extra tarp/poncho, groundcloth, etc.
I've slept with a fleece inside my breathable rain jacket and woken up with a very damp fleece. The next night, in almost the same conditions, I wore a t-shirt then rain jacket then fleece on the outside. No dampness on the fleece and I was much warmer.
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