The video on the left is from the early 2000's of pop singer Justin Timberlake tracking vocals. First they have him listen to the part he's about to double, then he starts tracking. Pay attention to how he aligns the vowels and vibrato when he doubles it. He is a tank, going for it and adjusting as he goes through until it sounds like there's barely a difference between them. This is the goal. Sometimes this is what it takes to get it right. Don't be afraid/discouraged if it takes a long time.