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How does old man Steve end up in the same reality
The moment he goes back in time and chooses to stay with Peggy that's a new reality, no?
He didn't change anything by going back, so no alternate reality was created. Cap was always destined to go back in time, marry Peggy and stay there. You can tell this because when Old Cap shows back up he doesn't come through the machine. He just shows up at the time and place he left from originally.