I understand and agree what you are saying until you said this: "The crucial thing is that if my assessment is that with all the eggs in 1 basket my risk is lower than with the eggs in 20 baskets then I will stick with that one stock."
Having everything in 1 stock does not reduce risk.
If you mean that you have only x% of your net worth in 1 stock and you have the balance in cash or a home or under the bed,I see what you mean. But if you have 100% of your net worth in one stock because you feel that your risk is lower being in that 1 stock you are not lowering you risk that way. Other than this one point I agree with what you have said. Second. Can you also explain what you mean when You said (Gut Feelings can be automated).