I just got back from buying a bunch of lambswool/merino sweaters from Value Village tonight, so I'll have a hard time ever giving that up.
Think of a deer's natural waterproofing system: They do not have a waterproof shell layer outSIDE the insulative layer:
1. skin (waterproof layer)
2. fine, dense hairs (windproof, insulative, & water-resistant wicking layer)
3. longer, thicker, less dense hairs (less insulative; more evaporative)
If you've felt the coat of a dog or a cat that's been out in the rain... even if their outer hair is soaked, rarely will the dense hair next to the skin be soaked.
I believe that's how the softshell systems work. The problem is, the ones I've seen aren't very quiet, though - certainly nothing like wool, but they are stretchy and form-fitting. (I wonder how I could make my own...)
P.S. I like your quote, Jimmy. My boss always says, "Anything worth doing ...is worth overdoing!"