All the experiences listed, I've experienced - which probably has a lot to do with why I am a skeptic.
I would add to that list "learning about human psychology, especially how memory and perception are altered by expectation, desire and suggestion, and how we can be selectively blind to things that don't fit our preconceived notions, and conversely overemphasize things that do."
I think this learning is very conducive to the fostering of healthy skepticism, and humility about one's own unavoidable biases.
For this purpose, I would recommend for ANYONE the book "A Mind of Its Own: How Your Brain Distorts and Deceives" by Cordelia Fine.
Why I'd recommend this over books that are specifically on skepticism, is that it is very accessible, written in a conversant, entertaining style, not very long, yet absolutely packed with case studies demonstrating the quirks of human psychology. A great read, and I don't think that even people who aren't science-nerds like me would find it anything but that.
I'm glad you mentioned skeptoid, by the way - that's one of the best (if not THE best) skeptical podcasts out there, I think. Brian Dunning does an awesome job with it - his examinations of various subjects are always thoroughly researched, and thought provoking.
Here's the link for those who are intrigued: http://skeptoid.com/
A skeptic is a person inclined to doubt all accepted opinions, and today the word has strong connotations pertaining to atheism and agnosticism. In this essay, however, skepticism is only the ability to take all factual proclamations with a beneficial amount of salt.
A healthy degree of skepticism can come about in two ways: naturally or logically. Note that these two paths are not mutually exclusive. This essay will only focus on natural skepticism because it is far more powerful than logical skepticism. By definition, however, it only comes about through life experiences. The goal of this essay is to lay out the necessities for emulating the causes of natural skepticism through entertainment. Before learning what to think, one must learn how to think.
Natural skepticism is more potent than logical skepticism because it invariably becomes intrinsic to a person’s reasoning. Instinctive and natural, as opposed to logical, skepticism of the stories and evidence of pseudoscientific claims is more likely to prevent waste of resources. Most importantly, increasing society’s degree of natural skepticism is more effective in increasing skepticism of religion.
The following, to start us off, is a list of experiences that may produce natural skepticism in people, with varying specificity and hopefully a semblance of order:
· Examining arguments for skepticism. (as noted earlier, they’re not mutually exclusive)
· Learning that a practical claim learned from a close friend or relative (who usually heard it from a close friend/relative who usually heard it from a close friend/relative) is false when tested. This is the purpose of the TV show “Mythbusters” and podcast “Skeptoid”, and is why scientists, with their constantly changing fields, are usually skeptics.
· Learning that a statement or preconceived notion that has been accepted and followed unquestioningly for a long time is either false or holds a far deeper meaning than previously thought.
· Learning that a part or the whole of the religion that has been believed in (having followed it is optional) for a long amount of time is false. This is why it is difficult to find a non-religious person believing in pseudoscience.
· Learning that a story that was accepted as true is false.
· For learning that X which is A important and accepted B strongly for C amount of time is false, skepticism is increased by A * B * C. The corollary, for learning that X is true, is that skepticism is slightly (A * B * 0.2) decreased. These equations are arbitrary; anyone who wants should attempt to come up with a full mathematical system.