I first encountered Settlers of Catan visiting my out-of-state friend Doug. It would actually be a while before I'd play again or really get into board games but that was the very start. And when I did start really getting into the newer board games, Settlers of Catan was at the forefront.
As I commented before, Settlers of Catan was a lot of people's introduction to designer games/Euro Games/German Family Games when I first got into myself. I wonder if that's still the case or if there's another new entry point. There are a lot more games out there and a lot of good ones. But Catan has also reached the point of being mainstream. Worldwide, really. It is still a good game, one I still play when I can.
Over the years, it feels like I've seen a lot of Catan hate in the actual community. Some of it, I think comes from the same kind of thinking that when everyone starts liking the band that no one ever heard of, they stop being cool.
I also wonder if the fact that Catan is fundamentally a family game is another reason that some folks have issues with it. Because while there are ways of attacking each other and it is anything but a cooperative game, you still have to interact and get along with each other well enough to pull off a least a couple trades. I have played with folks who could keep a mental spreadsheet going that I would need excel for but who couldn't trade for beans.
I haven't heard this old saw in a long time, the idea that non-gamers would compare anything they'd see you playing to Monopoly. (So, Twilight Imperium? It's just like Monopoly, right?) My favorite experience like that was someone watching me teach Zendo and saying "So it's like Mastermind but with Tetris pieces" to which I replied "Exactly" since that was a pretty good call.
But, in many important ways, Catan is like Monopoly. If you play Monopoly as a trading game about infrastructure development, that is. If you play Monopoly as 'roll the dice and go round and round the board', you just like hearing me scream.
Still, all the things that make Monopoly actually worth playing (developing an infrastructure, wheeling and dealing as you trade with each other, the dice making everything uncertain and exciting) are in Catan, without the stuff that makes people burn bundles of Monopoly in a bonfire. That's part of what makes it accessible.
At the same time, Catan was the first board game I ever played that was truly inclusive. Between the possibility of being able to get resources on anyone's turn and trading, Catan does a good job keeping everyone engaged all the time. No long waits in between turns where I can go and make myself a sandwich.
I think Catan's true strength and staying power is that it is fundamentally about interacting with the other players. On the one hand, you have to get along well enough to make good trades. On the other hand, you have to be prepared to stomp their faces into the dirt with the bandit and monopoly card and cut them off. That's a pretty high level level of interaction within a pretty simple set of rules.
Settlers of Catan is a milestone in boardgames. It really did change the hobby. But, more than that, I think that it is a game that still has the place in the world and in a lot of people's collections.