For instance, it is very common to use income as a proxy for your economic success, and then to group people into quintiles, calling the bottom quintile "the poor". It seems reasonable, but it's wrong enough to lead to very wrong conclusions. A college student living on their own will appear to be a "poor household", even though many are likely to be in the top quintile later on in their life. These scenarios seem like exceptions, but when you add them up (as Dr. Sowell does), they show a very different picture.
Following people (statistically) through their lives, and across generations, is a common theme in his work. It's harder to get good data than the snapshot-in-time approach, but he does the work, and it's so much more informative.