@Big_Boss My colleague who typesets this raised objections to my view similar to yours and this is how I responded:
"Even conceding that you're right doesn't change the fact that since she hasn't told him how many times he has to avoid death to go on living in that body (i.e., how many different endings he has to probe before finding the one in which he survives), in practice he will experience anxiety over not knowing. We've already seen it in this chapter: he considered maybe thinking of looking for a girlfriend, but decided against it because he feels the mere thought of it means death is probably approaching. This implies he has an inkling that Death is a sadist who dangles the prize just out of his reach. Given that some of his deaths have been pretty pointless and out of the blue (the magician, the car crash, the gangster, the delinquent), I can't blame him for thinking like that.
That thought alone seems enough to make any hypothetical situation in which he manages to stay in a body an impaired life."
So I agree with you. Death may not be playing with him deliberately. But the vagueness of the terms of his punishment mean in practice he's likely to become paranoid. Wouldn't you?
There was a film in a horror franchise which had a slightly different premise whereby Death personally went after people who had escaped the death that had been originally "planned" for them. The person who survived the longest did so by checking herself into a psychiatric clinic and living her days (years) inside a cushioned room. I believe this is becoming a factor in his mind.
As for your question… I think this is one of the stories where we savour the journey rather than wait for the ending. I like following his thought process and seeing how he changes with each experience. I doubt a great philosophical point will be unveiled in the end. Personally, I doubt he'll revive in the end in his original body. I think the series will end with his going on to stand before the scales and being dispatched to another plane of existence of reincarnation or whatever. I also think he'll spill the beans to his mother and leave his regrets behind on his last life. Not sure whether his ex-girlfriend will feature in the story, but perhaps he'll take over her fiancé's body.
Just my two cents. We'll see.