As for 'dice rolls', it depends. In climbing there is "objective danger" - danger you cannot really control, like your route passes under a serac that collapses frequently, and "subjective danger" that you can control - you step on a loose hold and fall. They spend months planning, trying to reduce the objective dangers as much as possible, and of course years of training to reduce the subjective dangers. Summarizing all of that as a 'dice roll', while it might capture the percentages of particular high risk climbs, seems to miss the mark a bit. Spend a night in a climbing hut, or hanging in a tent/portaledge off a mountain side and it's endless talk about this sort of thing. How to master your body, the terrain, and often most importantly and hardest, your mind.