On the face of it, this is an idea which sounds good.

Regrettably, it runs afoul of a stumbling block common to too many proposals for improving the Monastery: who will do the work... and with what guidance defining a "Most Insightful" post?

On some of the factual (but more-or-less arcane) discussions of perlguts we don't seem able to achieve agreement on what's fact vs. what's misconception. Something as inherently subjective as "insightful" would -- IMO -- be a far larger challenge.

Update: Browsing "Selected Best Nodes" doesn't guarantee you'll find insight (some of the posts there earned their reputation for clear exposition or clever algorithm, and some may even be inaccurate) but the list overall surely includes enough highly rated posts to keep a reader busy or amused and, at least occasionally, blessed with insights.