Every record you read, every clue you interpret, every family you analyze is done through your own modern-day perspective.
Have you tried and thought about how your ancestor's life experience might have impacted his decision making? Have you thought about how your ancestor's educational level might have caused her to react to a certain situation?
Have you thought about how your ancestor's childhood might have skewed his vision?
But when you do all this thinking, don't forget that you might not really be smarter than your ancestor.
We may live in different times, but we might not always be smarter.
Just something to think about. In some ways our experiences may be different than our ancestor and in some ways they might not.