I'm not thinking primarily of transactional emails here. If Gmail allowed dots and allowed registering both "jane.smith" and "janesmith", Jane Smith would be we

I'm not thinking primarily of transactional emails here. If Gmail allowed dots and allowed registering both "jane.smith" and "janesmith", Jane Smith would be well-advised to register both, because it's going to be the most common mistake people make. It's the same principle that suggests that if you own a .org address you should probably go ahead and buy the .com, too.