My friend’s father introduced me to Settlers of Catan about eight years ago. It’s my most frequently-played board game, mostly because I’ve owned it for so long. I’ve probably played 40 or so games total in those eight years; if each game is about 1-2 hours, that’s a fair amount of time spent in the pursuit of brick and sheep.
That said, some other games I own I’ve played less than five times each. The difference in my approach to those games and Catan is significant; I play Catan with a level of natural understanding far different than the other games I play. And while I still lose (on occasion), I feel like I have a fuller grasp and appreciation of Catan: minor choices become critical, incremental choices add up easier to a long term goal, movement from other players signal much more than they did before, and I can usually tell which turns will net me a win or loss.
There’s been some recent discussion on the difference between a game played deeply versus one played less, corresponding for a desire to examine and understand board games more rigorously. A recent forum post by user MiloMilo122 on BoardGameGeek about a “100 Play Challenge” proposing that gamers to play a board game 100 times to see if they arrive at a new or deeper understanding of the game. 100 plays may take some time, but I’ll always have Catan around, so maybe one day I’ll reach it.