It sounds like you had a good father. A good father is proud of children who developed their own sense of integrity, and live by their own standards, even if they are not quite the same as their father’s.
Your father made mistakes, and quite possibly asked himself the same questions, wondering if his father was proud.
Your father has very good reason to be proud of you. Regardless of the mistakes you may have made, you are willing to look within and face yourself honestly. Your life has been much different than your father’s. No doubt, the two of you have made different mistakes. Odds are that you have different aptitudes/talents as well. My dad was wonderful with math, and I was awful. When it came to fixing things, my dad was all thumbs. I’m just the opposite. Your dad grew up in a far different economy, so money management and livelihood related decisions have to be different for you.
He would not want you to imitate him. You can have some important values in common, for example honesty and compassion, but you must be your authentic self. Some of the stuff you do or have done, he might never have agreed with. If you were the father and he was the kid, no doubt he would’ve done stuff you didn’t agree with.
If your family is typical, sometimes your wife is more proud of you than she is at others. Sometime around the age of puberty, your children are likely to decide that you are lame and out of touch. In a way, they are right. They are growing up in a different world than you did. If you accept that, and avoid comparing your past experience with what they are going through now, they are less likely to think of you as lame and out of touch.
A couple of decades from now, they are likely to respect and admire you very much.
It’s wonderful that you had a father who’s thoughts were important to you. My dad drank so much that sometimes he couldn’t remember my name even when he was sober.
Another reason for your dad to be proud is that you love your family very much, and are there for them.