Yeah, what you have to remember is that most users are pretty dumb. They don't know how the software works, just where the buttons are to do the thing they want to do. They don't read anything or learn anything other than what is needed for some menial task, and that they're only employed because the company they work for is too small for it to be automated.

If your stuff is free then do what you want, but the second you start charging money for stuff, you have to be acutely aware that the change that makes sense and makes everything neater and cleaner is going to make some 65 year old in an office freak the fuck out because now they can't do their job because their buttons have moved or the icon has changed.