Who ARE all of these people I’m apparently related to?

My wife’s mother’s family, the Olins, have been doing family reunions for decades. As I first mention a lustrum ago, one can trace my wife’s ancestors nine generations back; unfortunately, a couple of my mother-in-law’s siblings have passed since then.

Whereas, on my side, there have been these intermittent attempts to gather Yates (mother’s mother) and Walker (father’s mother) families together, with no real sustainability. My mother’s father’s people, the Williamses, have been doing a gig in recent years; these are people even my mother hasn’t gotten to know until fairly recently.

1. Have you ever gone to a family reunion? Is it a regular event or a one-off? If you haven’t, would you? Why or why not?
2. How far can you get in your own genealogy? I can find my mother’s ancestor five generations back, but am still unclear as to my father’s father’s side.