After my experiences this year I'd never use a down woobie. We had a lot of rain with some hail and a little snow one night. It was so nice to just throw my Kifaru woobie over top of me and stay warm. One night when it was really bad the other guys were a little worried about me because they had all gone back to the truck early due to the weather and I didn't come back till normal time because I was quite comfortable. We'd get back to camp and I'd just hang it up and it'd be dry by the next morning after being thoroughly soaked to the point it wasn't even really keeping me dry anymore but at least I was still warm. DWR only goes so far.
I wish I only had a size 14 foot. I have a size 13 with a 6E width, so finding shoes is also near impossible. It's always great when you go to the specialty stores and still only have 1 option.
It doesn't sound like you're talking about a sleep system. My down bags stay in my meat baggie until my tarp is pitched. No way for them to get wet, unless my backpack takes an extended swim.
During the day time I use different/multiple layers of insulation if it's cold. I still never let my insulation get wet. If it's precipitating, I have rain shells on. Worked great for me for 20+ years of hunting coastal Alaska.