The military chute he used was a four line release, correct? Essentially, after you deployed, you pulled the lines from the canopy, grabbed those lines and wrapped them around your hands and those become your steering. You pull down on the left or the right and it pulls the canopy down and distorts it so it turns in that direction. It wasn't a perfectly efficient system and it was standard practice to turn into the wind so you wouldn’t be running with the wing when you landed.
So you have to assume he was able to release those lines, wrap them around his hands in very cold temperatures with no glove on, and turn into the wind. All at night in 40 degree weather. In your opinion, wouldn't his hands have hurt from the cold and made it difficult for him to hang on to his steering toggles?
Secondly, you say that the weather, the night jump, the unfamiliar rig would not pose a significant risk to his life. Would that be dependent on his skill level? Suppose he's a complete whuffo? Or someone with a handful of jumps?
I don't think there is anything known as a "four line release" parachute canopy.
Indeed there is a four line release mod on some round reserves. I don't think Cooper's chute had it though. I think he just had a no-mod, non-steerable, don't-bounce round. 377 would more accurately know. On the four line release, after you open there are tabs or pieces of line on the risers that you pull that release the four rear-most lines of the canopy. That allows the back of it to rise up into a bubble like configuration. That allows air to escape out the back, creating some forward drive. The next outward lines have toggles attached for steering. Sure it's preferable to land into the wind if you can tell what direction that is, but I think whatever control he might have had would be best served to avoid obstacles and get into a decent landing area. Robert, I've never heard of that four line setup you described. That must be old old school military. That apex hole at the top of a round is what reduces oscillations.
Yes, cold hands are a bitch and they hurt. But hopefully if you put yourself in a situation like that you have the focus to differentiate the nice from the necessary. Warm comfy hands are nice. Exerting whatever control you might have over a parachute is necessary. And we don't know that he didn't have gloves. He could have had some in that other bag or in his pockets.
Obviously having some experience would help him. But I don't think a lack of it is a huge threat to him. You get off the plane, you pull the ripcord, you land somewhere. Again I would cite Andrade's research, and the subsequent similar skyjack jumps.
