@Carl Hancock - It's not complexity that has all of a sudden emerged, it's additional features like Post Formats, and others that have compounded the simplicity over time. You make a good point in that if you take all of the extra stuff of WordPress and throw it out the window and leave it as Barebones, then getting WordPress up and running to post content is still relatively easy. But once you get past that, things go downhill although over the years, WordPress has taken the pain out of having to use FTP to update themes, plugins, and WordPress itself.

I think some of this complexity that I am seeing is partly due to my communication skills. If I can't explain something within 5 or 10 minutes, then I think it's too difficult or complex. I found myself taking a long time to explain why they needed to sign up to WordPress.com, API keys, and what have you. An example is right out of the gate for security reasons, explaining to them why they need to create a new user account, assign that one admin capabilities and remove the first account they created. Why can't that step be part of the install process, they have to create an account anyways.

I will try and use your iOS analogy the next time I'm in a position to explain WordPress to someone new. It sounds like a good one.