Definitely an interesting article.
Based on what you are saying, I end up thinking of 3 buckets:
Some of your items could fall into the first category, but I don't think all of them would. Is your reduced trust in any specific system due to a value (item 3), or based on results of your actions?
I think the key might be to develop methods of measuring your sanity.
I have often questioned my judgement when in disagreements. But it is hard to tell if judgement is good or not, especially if all I have to measure it is my opinion.
But if we measure the value of judgement or wisdom based on the results of their actions, then it is not as value-driven. Of course measuring results is still subjective, so it needs to be compared to what the intended outcome of the action was as well. Additionally, we would need to obtain a large enough sample size, otherwise we could conclude that lottery winners have better judgement than lottery losers.
Actually now that I think about it more, the second half of your article sounds like you are more concerned with your beliefs more than your heuristics. I am not sure if I would consider beliefs a component of wisdom, but I am not opposed to the idea either. I could believe in a flying spaghetti monster and still have wisdom. Though that example is not a proven fact, just something I believe.
Edit: Also thinking about it more, there is the decision between tools of perception, option generation, decision making, and implementation. Maybe the problem is that wisdom consists of so many sub-topics.