Death had always been Voldemoort's weakness. For some reason the Dark Lord had continually out ran death until he'd reached a point where death could not capture or taunt him.

There was always the question as to why? Why live forever? Why, constantly, try to defy fate?

Why was it worth it?

Harry was determined to find answers to the questions as he asked ones of his own. What would
it be like if I died? What would it be like if Hermione or Ron died?
What would I miss that others would experience?

He thought that one most closely related to Voldemort.

Was Tom Riddle such a glutton for knowledge even now? Was he afraid to miss something revolutionary? It would be typical of the stupidly intelligent genius that was for sure.
He thought of all the things he'd miss. He could think of three.

Ron. Hermione. Voldemort.

It was amazing how he was back at square one and maybe even a little bit in sync with how Voldemort's thought process worked.

Did he really want to miss out on his best friends' kids growing up and having kids of their own? On them getting their jobs at the Ministry? Or seeing whether Voldemort was defeated or reformed?