Thanks Eric. Yes, I agree that knowing the limitations and proper use/care of each piece of gear, especially critical ones like a sleeping bag, is crucial.
I've experimented with MYOG VBL's a few times, and though they get clammy, my insulation stays dry and I'm warm. I think I'm going to get a silnylon rain suit next winter. Relatively light and will keep my insulation dry. Cuben would be nice for the weight, but I'm not plopping down the $$ for a cuben VBL that I'll only use a handful of times each year.
My wife usually comes backpacking with me, and in the exact same conditions, her bag is never damp. The only difference is her and her bag, which is a Montbell SS #1.