One of our startups just did launched several high-profile retailers onto Foursquare, gowalla, mytown and others with great incentives for checking in... and the check-ins were simply too underwhelming too continue with the program.
It is going to be darned near impossible to come up with a service that will get the needed critical mass. Facebook is the likely service to use, but people aren't flocking to check-ins there either.
And this legend in the making needs to lose the hideous glasses. It's not a good trademark.
There, now I can be positive for the rest of the day.