I know it’s early, but I’m dreading this based on what I’ve seen. 95% of the users I train are someone in a small business who has been tasked with dealing with the website, and the level of experience they bring to it is a basic familiarity with MS Word and Outlook. They get the toolbar layout immediately. Trying to get the average person who uses WP as a CMS an hour or so a month to understand this is going to be a problem.

You know what would be really nice? I simple checkbox next to the gear icon in the link dialog. That way I can train users by simply saying “if it needs to open in a new window/tab, check here.”

That’s usability I can make hay with.