I think user generation is the key to solving the local search issue. I think with user generation we get a complete product and additionally we are starting to see that with Yelp. In terms of monetization, we will start to see that in the next few years once a model takes hold. With the advent of video on sites like Jippidy.com, the potential for monetization increases.
Great list, we've made a video for one of the spots on your list "21st Amendment". So if anyone wanted to get a good feel for the place, feel free to check it out.
I love Craigslist, even is today's web 2.0 world, its still one of the most useful applications out there. It can help the consumer as well as the small business owner.
Local search is getting very exciting. In the next few years we will some killer apps and eventually a winner in the space. I think this is just part of figuring it all out.