In order to qualify as a judgment, an affirmation must aim at getting it right aptly, through competence, and not just through a lucky guess.

Normal adults can doodle, amble, and drift with no need to assess risk, since there is normally no risk at all. Jazz improvisation seems less subject to standards of risk than surgery, and less than much formal athletic performance, as in a tennis match.

There's not much to be done about the impossibility. One must instead get rid of the desire.

There isn't a formal definition of success.

The concept of intuition is more often used in philosophical theorizing than is the concept of observation in scientific theorizing (proportionately). One reason is that there is (proportionately) more ostensible conflict of philosophical intuitions than there is ostensible conflict of scientific observations. So much for the use of a concept of intuition in philosophical theorizing.

It is also certain that when we assent to some piece of reasoning when our perception of it is lacking, then either we go wrong, or, if we do stumble on the truth, it is by accident, so that we cannot be sure that we are not in error.

There is no need for the scientist to go into whether an observation was made, nor into the who, what, when, or where. The data on which scientific theorizing is based are rather the propositional contents of the instrument readings recorded, or the facts detected thereby.