And on that note, I think part of the problem with community nights are multiple. I'll list what I think are all factors.
1. Fractured base. People are split across multiple timezones so there's never going to be a perfect time of when to make the community night.
2. The community is ever changing. The prolific posters we had 8 years ago are not the same prolific posters we had 4 years ago who are not the same prolific users we have today. There are a few stand-out names that have continued regularly across that span but I can see it in the mafia games for instance of the ever changing wave of people.
This in turn makes it hard to keep the same connections and it also makes up part of a larger question, what is "our community"?
3. Taking a look at the 3DS Friend code, from a quick rough estimate I'd say 15 - 20% are names of people I recognize. The rest are people who posted their code but have shown up nowhere on the forum or at least any thread I can remember. Think to of the stationary thread. Tons of codes by brand new people who then promptly disappeared when they got what they wanted. So, if only 15 - 20% of the people are regulars, even at 100% participation by those people, it's still going to be a low number.
4. Not everyone is going to have the game that is being played that night but that's something I'm sure is expected.
5. People may not have an interest in online play. I, personally, dont. I'm a single player type of gamer. It was interesting when Mario Kart DS came out to try it. But it soon became broken with people dropping out so as not to have a loss to their record and snaking. I played one battle of Advance Wars: Day of Ruins online with somebody here but that was years ago. And I can't really think of much else I might have done aside from trade some tickets or something for Metroid Prime 3. Generally, if I'm using online play, it is because it is necessary to so that I can complete a game 100%. It's selfish I suppose but if I'm playing something multiplayer, I'm doing it with people in the same room as myself. It's a lot more fun than the silence of playing online with no around. It's silent because I don't want to hear some bonehead cussing and swearing constantly because that's "smack talk."
6. In the same vein as 5, there doesn't seem to be any benefit to it. I think you usually end up with more negative experiences sometimes than positive. But maybe I'm just being a pessimist. Yes, playing against real people is better than a simple A.I. but I guess I'm satisfied with the challenge the game offers on it's own and when I do play multiplayer, like I said, I prefer to do it with people in the same room as me becuase you can do more than just play games at the same time. It's more of an event I guess.
Anyways, that's my thoughts on the matter and I know everyone has their own views so don't let mine get you down.