I just read all the posts here as I am also planning a city site with a cityname.info domain name. I've gone through all the thinking many of you here have. But there is one thing not talked about much that I'd like to bring up.
My understanding is that sites do way better in terms of advertising clicks with visitors who happen upon your site through search engines, than do a community of users that use your site on a periodic basis for a directory or social feaures. The city I am going to do is not only a community, but it is also a year round travel destination. So, I'm thinking I want to get those searching for destination information to find my site when searching for information. What's the bet way to do this?
I think perhaps the best way is to have hundreds of informative articles on activities, regions, lodging, restaurants, hiking, wineries (we have 150 wineries), beaches, etc. Almost like a very free-form magazine. With a major university in the town, I'm sure there must be plenty of journalism students that would write these articles pretty inexpensively (I'm not worried about spends $XX,XXX on this project anyway). If the site were massive, with lots of great information, and SEO'd perfectly, it's bound to move high up in the search ranks. And those searching would be very inquisitive and thus likely to click relevent ads. Once the site gets good traffic, local advertisers would come into play.
As for the software, I'm thinking that perhaps an Article Management script would work well. I have seen some from InteractiveTools.com, Interspire.com and others. Although, a pure article management script could limit me in terms of adding things like an event calendar, reviews, etc.
Could I get your thoughts on all this? Appreciate it.