Rather I am (more or less) content to accept a game I choose to play in the state it's in (assuming I have no control over its state).
Rather I would say there are some people who cannot turn off their competitive urges for something as inconsequential as a game.out achievement, goals, and conquests. Moving backwards or starting over to these people is not fun. I would place Kylani in that group.
But if it's not fun, then indeed, yes, he should stop doing it.