Ahh, the lawyers at Skype screwed the pooch. I am actually on their side in this fight, too. I know that they need to protect the trademarks otherwise they’ll lose them. At Microsoft the lawyers would do stuff like this from time-to-time (my friend Robert Mclaws told me recently that the Microsoft lawyers are again going after some community members who’ve taken on trademarks too closely).
What should have happened? A licensing deal that doesn’t cost much. Say a buck a year. That way Skype would have been able to shut down bad uses of the Skype trademark, while letting community members who are helping its ecosystem out stay up.
Worst case? Sites like this should be shut down by lawyers when they pop up, not years after they become popular.
Personally? I’ll never start a community site with a trademark in a URL or a name. I know that the danger of getting a lawyer to jump on you is way too high. This isn’t the last time this will happen.