This is exactly what shapes the areas of success for OSS. It's glaringly obvious looking back, that success perfectly matches the motivation of contributors in different areas.
And that said, it doesn't need to be so difficult to include all these pesky checkboxes in a way that they don't confuse or hinder usability for n00bish users. This used to work for Gnome 2. Never met anyone who thought Gnome 2 was too hard or counter-intuitive, they were just more or less used to it. Windows XP and Windows 7 have a lot more checkboxes if you look for them.
Sorry, gnome 2 was hardly 'easy', which is the bar that modern, commercial window managers are setting. 'Not hard' and 'not counter-intuitive' doesn't cut it any more for the bulk of users, who are less savvy than previously.
If there's one thing that Apple and even Microsoft are showing with their window manager and widgets, its that simpler is better, and we've been missing that all these years.
I had to walk my 80 year stepfather through an OSX install yesterday. He would definitely have failed if I hadn't been there (he still got stuck for five minutes on the gesture screen (or whatever it was), which neither us really got). He's used Macs for years - without being a power user of course. I don't think Mac are getting easier. They're getting harder to use but more "impressive", more filled with theater. And sure that's the "bar" that modern OSes are "setting". If open source follows in those steps, it certainly will be lost (and it's stumble a few steps down that well already).
Whether you call Gnome 2 hard or easy, it's main problem was that it's configuration apps and menus were confusingly organized. If the incremental improvements Ubuntu was making could have continued a few more years, things might have been great. The decision to create "Gnome shell" probably forced Canonical's hand but Unity also seems terrible to me.
And that said, it doesn't need to be so difficult to include all these pesky checkboxes in a way that they don't confuse or hinder usability for n00bish users. This used to work for Gnome 2. Never met anyone who thought Gnome 2 was too hard or counter-intuitive, they were just more or less used to it. Windows XP and Windows 7 have a lot more checkboxes if you look for them.