Mike - You bring up an interesting point. In terms of the new domain extensions, I believe few will succeed in the long run. A big hurdle is that extensions that are too similar to each other, like .photo, .photos, .pictures, and .pics, make it impossible for people to remember a company's domain name.
If someone advertises "Sarasota.pictures" through other media, a huge amount of people will just go to sarasota.pics, sarasota.photos, or even sarasotapictures.com.