I like OS X but it reminds me of Ubuntu sometimes. The kind of OS that wants to do everything for you, the kind that sort of dumbs you down.
But OS X is clever because the user-friendliness mostly surpasses the alternatives. IMHO, something like Debian is a better OS but nowhere near as easy to use, regardless of your previous experience.
I would agree that Debian is more difficult to use in general, but I am not a fan of OS X. I am not a fan of Apple/Mac in general. I don't agree with their business model or how they treat their customers. I also, as a general statement, just don't like how it functions.
Ubuntu is fun to mess around with on occasion, and a great intro to new Linux users to see if they can muster switching from one of the big two, or big three as it were these days (Mac, Windows, Android.)
I think #!, if it installs properly and with no strange hardware issues (which are of course bound to happen with any distro) is user-friendly
enough for new users who only require very basic functionality. I'm talking office software, web browser, media player, which seems to be the gist of what most people use these days. I've let a couple people use it who otherwise have no Linux experience, and little otherwise technical experience, with little issue.
It comes with a script on startup that asks very simple 'do you need this functionality? y/n' questions which I think was brilliant considering it runs openbox, with which a surprising number of people are still unfamiliar.
Plus it's got all the commands on the side to help new users, though it doesn't explain what a super key is, which new users find confusing.
I sound like a bloody spokesperson. xD