Skepticism requires critical thinking and engagement. You can't be a proper skeptic about something without taking the time to understand the domain you're being skeptical of, approach it in good faith from first principles as much as possible, and accept criticism in kind.

Most people just won't bother, because cynicism and snark provide a better endorphin hit, and the internet has trained people to associate that feeling with likelihood of correctness (what Stephen Colbert called "truthiness" back in the day.)

the first things skeptics should be skeptical about is skepticism itself: are they right in being skeptical about what they are skeptical about?

The first thing skeptics question are sentences which begin with

>> the first things skeptics should be skeptical about

from there I guess we just migrate up to talking shit about bloated blog posts where one dude mumbles his observations about deep thoughts.

If in their analysis, they come to the conclusion that they shouldn't be skeptical, does that make them the best skeptic or the worst?

the best if their skepticism is carefully done.

Yes, I completely agree. The author should have applied it to his "odds of success vs extent to which you consider second order and subsequent consecuences" graph and saved everybody the time.