If I am only going to be stroking for a little while, I will go dry, but for the times when I feel like stroking for a half hour or more, I often use lubricant. I am cut and don't produce much pre-cum and I do enjoy the more smooth, sliding feeling on my hand and penis when I use lube.
It depends. If I edge for awhile I can see the precum leaking out of the tip of my cock. When I can't take it anymore and I really get to stroking my cock full length my precum gushes out enough so no lube is required...
When I jerk off, I like to grip my dick and pull, more than slide in and out. I do like to use lots of lube sometimes, like playing with toys or for just a different sensation. But I like the feel of my real skin in my hand. I never find much chaffing at all, though some days I may come 5 or more times.