Some people just need to see things a specific way, or they are totally lost. I know people that couldn't work an upside down door handle. Please never let that difficulty drive Linux development. Fortunately, Linux has always been about options. there may be a distribution out there that is for people that can't find their car if it is parked on the wrong side of the driveway (I think it was called SugarOS), but I believe it will be an evolutionary thing. Kids today are starting at very young ages with much better technology and are getting more intimate understandings. Kids are reaching competency and proficiency very quickly like kids do with anything they can actually get their hands on. Most adults if, say, they were pasty the age of 20 when they first got introduced to a computer, without much concerted effort, ever become more than very well trained novices. For anyone familiar with learning theory should understand that with that type of 'experience', it can't be adapted, no step or detail seems any more 'important' than any other in accomplishing a task, they don't see see the big picture, and the challenge in learning anything new is equal to the number of new steps to memorize. In what way is Linux ever going to be easy for these people to learn, and in another way, the kinds of challenges Linux can deal with, the tools are virtually worthless to a computer novice, those that don't see it holistically.
I think this explains why it is easy for little kids to use Ubuntu. The learning curve is great with just a few bumps, but while the system isn't designed to limit out at novice use, there are plenty of tools and methods to let novices work their way through the system doing basic tasks till they get a better understanding of all whats going on.
Tasks in Windows are just as simple in Linux for a novice, but the methods are different. The big difference between Linux and Windows, for me, is lifting that ceiling. If you begin to understand what all is going on or how things work, Linux gives you new and creative ways to do complex things in very simple, non-obvious ways. This is where I think people get intimidated. A novice watches a proficient Linux user do something seemingly "magical" and the novice begins to believe that is the way they need to do things. While maybe it should be the way to do things, that doesn't mean it is what they need to be doing right away. Linux is a world of possibilities: Be aware of where you are in your understanding with your computer and take appropriate steps to learn things in a way that is appropriate for your level. And if someone that helps you works their magic in ways that are beyond your level, don't worry, it probably took them some time to get to that level themselves.
However, if you really don't care to put in the mental effort to get past novice, I recommend getting a Macintosh. There are fancy expert features of OSX, but they are kept pretty hidden as so not to appear confusing.
It is a lot like a high performance car and their maintenance. Drive it hard, and it is going to need more work. If you need to hire a mechanic every few hundred miles, it is going to be very expensive unless you do your own mechanic work. Some people need to be rich, some people need to be mechanics, some people need to learn to drive carefully, and some people just need to buy slow cars.
Windows is like riding the short yellow school bus; it gets you where you need to go.