Well if Europe is all you are planning to tour, you don't really have to worry about a breakdown because help is always nearby in the form of other motorcyclists or service stations.
As for your other questions. Some people have the skills, some don't. To someone like myself, mechanical devices are plain and simple and to others, a nightmare. I gained most of my experience from reading technical books at a very early age. I also perform all maintenance and repairs, mostly because I want the job done right.
You can either gain mechanical skills on your own by getting a shop manual and then rebuilding a bike (chances are you'll learn from the mistakes) or by taking a course at a community college. Also, understand basic electronics. There are two reasons why a motorcycle won't run (other than the rare mechanical failure); fuel and ignition.
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