Personal opinion that the game is bad. It was the first German-style game people were exposed to, which meant it was compared to games like Monopoly and Life rather than other German-style games, which made it look good and catch on. Settlers is far too determined by early placement, has frustrating trading mechanisms, is diplomatic in bad ways without being diplomatic in good ways, and so on. Bottom line is that I don't find it fun or interesting.
Funny, I agree with every one of your criticisms after thinking about them a bit except your bottom line: I still find the game very fun. This makes me think Nomic will just be amazing.
(From Zvi Mowshowitz, leader of the New York group, and based on his experience)
Category 1: Discussions - The Base
A: Less Wrong topics. Usually recent posts. Often big hits.
B: Rationalist group planning and organization. Meta-topics. Dealing with group issues on occasion.
C: Spreading Rationality. Discussion of various approaches.
D: Contraband Topics. Discussion of things that I won't include here, but you can guess.
E: How To Do X, or how to do X well. Charity, meeting people, improving skills, relationships, etc.
Category 2: Presentations - Almost Always a Winner
F: Sequences. Andrew Rettek did these for public meetups, went over well I think.
G: Personal Projects: Variance, Geoff Anders's Psychology.
H: General Knowledge: CBT, Starting a Business, Basic Python.
I: Advanced Rationality: Attempted once, successful despite poor execution. Should be explored more.
Category 3: Game Nights
J: Proven Good Games: Illuminati, Poker, Citadels, 7 Wonders, Nomic.
K: Advanced Games: Much demand for general gaming, but not really that rationalist. Proven winners in this group: Vegas Showdown, Power Struggle, Baltimore & Ohio, Tichu, Through the Ages. I can keep going, many good choices. AVOID: Settlers of Catan (personal opinion) and Fluxx (cause you can do better, honestly).
U: Outside Games. Ultimate Frisbee is good.
Category 4: Other Celebrations
L: Karaoke
M: Baraccuda (bring something awesome you love)
N: Contraband Activities (enough said)
O: General Party In or Out / Pot Luck
Category 5: Special Guests
P: Famous Rationalists! If you get Eliezer or Robin or Vassar, you need no other topic. Probably a few others who get there on their own as well, or any generally famous guest.
Category 6: Self-Improvement
Q: Go out and do something to improve social skills.
R: Discuss or map out goals and plans. Set goals. Can be combined with other tasks.
S: Run experiments! For science!
T: Study Hall. Also folds into discussion of self-improvement topics.