Well, I use Ubuntu as my main OS nearly for one year, mostly for development and basic tasks like surfing the web. I have not encountered any serious problems and never had to touch command line to fix a issue. Of course, your experience may be different for your hardware and use case are different.

Most of the configuration is automatically done by installer in my case, but I don't know how yours going to be. But you should not worry about getting competent enough, I always google to find solutions and never try to memorize them, but one certainly learns trough the process as no solution directly solves a problem. :) As a side note, I don't think that we should not be our computer's masters to use them. I see these things as issues that need to be solved, and the community came a long way in usability terms.

I strongly recommend dual-booting with Windows. As you said, for certain things it just works and while most of the world use it, you will have to use it (at least in sometime). This will directly solve your third problem.