Ahh, the 3 W's. Yes, I take care of my Whiskey, Women, and Warm Stuff, in that order. Why?, you may ask. Well, no matter how much the shit hits the fan, the whiskey will keep me happy and at least lend the illusion of warmth. With the whiskey in good order, the women easily follow. And with those to to keep me warm, what does it matter if my clothes are dry or not?
Also, rolling is not a problem. I am a master roller (no, not that, Mike).
In the past, I've lined my big drybag with a trashbag which provides an extra barrier between the water and the goods as well as a medium for any water that makes it through the roll to condensate in.
I've got some good coldweather gear.
I guess the root of the question is that when packing to put your stuff in your kayak, do you go for compressibility, sucking air out for a tight fit, blowing it in for flotation, or absolute light weight.