So a second stage free-flow which is allowed to go on for as long as it takes to drain the air in both tanks... is that the only way that the diver loses all their air? I guess if their second stage starts free flowing while they are attacked by electric eels or something? A first stage free flow would take a long time to drain all the air which is why I think it's unlikely to be allowed to happen.
In the case of a first stage free flow in which the isolator is closed, the diver will still have 1/3 of original air supply available to him, so enough to get part way out of the cave and then switch to buddy's long hose.
Both first stages or second stages free flowing would also be a scenario in which all the air would be made unavailable, but that is incredibly unlikely isn't it?
So... silt out requiring a long search for the line, multiple regulator failure and eel attack seem to be the scenarios in which divers with mismatched tanks and breathing rates don't have enough air to get back out of a cave after turning at 1/3. I am sure there are other scenarios I am not thinking of. I personally am wary of going more than a couple hundred feet from open water and have never done so yet because I don't feel confident I have all the bases covered.