I read this today and thought I would share it with my fellow DPers. http://royal.pingdom.com/2009/10/09/the-top-5-tld-flops-ever/ I didn't know there was a .web or .aero. Either way, can you guys think of any other domains that haven't worked out?
As for .info failing the story makes a good point regarding registars basically giving them away for free. Now, everyone has seen the prices of .info climbing but perhaps this is more of a speculation bubble. I have seen no actual usage of this domain space by the general public since it's release. As for .mobi, casino.mobi sold a few weeks ago for something like $135,000. The mobile internet is the future and this name space has the best shot at capturing some market share.
Did I just read .museum? I have some domains shorter than that TLD... ...And who thought .aero would have been a good idea? Wouldn't .mobi cover most of these needs? All of a sudden I'm very interested in TLDs, always thought it was so peculiar to have to add ".something" to a url; it always made me try the .net and .org version of every site i visited back when I was just starting on the internet and actually had something fun and exciting to look forward to on these tubes. Alas, the internet has grown old, we need more .museums