Hopefully you will get some responses from members who live in areas that have more 'winter' than we do here in Tucson – but since you mentioned Trail Runners and Waterproof socks I thought I would share my experiences from last winter and a few hikes this winter.
I have used Seal Skinz branded waterproof socks purchased ~1.5 years ago with trail runners (Breatho Trail, Fellraiser, Superior, Lone Peak, Trailroc 245/255…) for around 15 hikes/runs at least partly in the snow, all 'day' hikes and probably nothing longer than 8 hours, mostly in what I think is fair to describe as very moderate temperatures.
What I found:
-The socks didn't take up as much room as I thought they would, but getting a roomier fit would be appealing for more frequent/longer/dedicated use.
-Either from foot sweat, leaking or water in from the top (when wearing 3/4 tights) my feet seem to feel damp after an hour or so (I have never tried to sort out which/what combination of those cause the dampness)
-I now wear a light or medium weight wool blend sock inside, the ultralight wool socks I often like to use feel wet too quickly and I like the extra insulation of the thicker sock
-The waterproof socks are definitely damp and in need of drying out at the end of the day
-In the temps I am in my feet are often damp but not so often cold with the light/med weight sock, ymmv esp. in colder temps!
It would be ideal if my feet stayed drier in these socks and it would be interesting to try other brands/models/systems – but I haven't been motivated to do that because this has been a good-enough-for-me compromise here in Southern Arizona and for the amount I hike in the snow I have not been motivated to tweak this part of my kit.
CM