On whether Cooper survived the jump...
On any jump made, the odds are against that the person goes in. But occasionally they do anyway, so I suppose anything is possible. But we don't know how Cooper fared, so we look at the situation and consider what is likely to have happened. Robert99 posted some scenarios that I think are unlikely. R99, I'm not bagging on you, I don't know you personally, I'm just giving an objective take on your suggestions.
Not necessarily. Cooper was a smart guy, I would guess that whatever he tied to himself, he tied tightly and securely. With the back bailout rig and the money tied to his front, that wouldn't have been too much different than the typical sport rig of the day, with a back main and front-mount reserve.
Freefall stability is kind of like learning to ride a bicycle, in that there is a subtle balance point to it. At first it can be hard to control, but once it 'clicks', it's really not hard. And like everything, some people take to it quicker than others. If he had prior freefall experience, the exit would not have been hard. And if he didn't, and he did tumble, again, he's a ballsy guy, I'm guessing he would keeps his wits about him enough to pull.
Not at all. Many people have deployed while tumbling and gotten open just fine. That spring-loaded pilot chute comes off your back quickly and takes the canopy with it. If you're gonna get tangled up in anything, it's most likely going to be the bottom part of the lines. And when the canopy opens, it's gonna flick you out of that like an errant yo-yo. You may end up with line burns, but you're most likely going to have an open canopy.
Parachute malfunctions are pretty rare. And of the malfunctions that do happen, total pack closures are very rare, and so are high speed streamers. Most malfunctions that do occur on rounds are slow speed, like line-overs or partial inversions. Maybe a bit higher rate of descent and less control than you might otherwise have, but usually survivable.
I think it's highly probable that he survived the jump. The concern I have, as I stated before, is whether he was injured on landing and able to hike out.