Just watching TNG's The First Duty again on Sky Something, and
realising: what did the Squadron hope to gain by executing an illegal
shuttle maneuvre for the graduation ceremony? Wouldn't they have
gotten into trouble?

No - if it had worked. Because it seems as if Starfleet Academy, and
Starfleet in general,  supports mavericks and rule breakers. Look at
Kirk's career: he cheated on his Kobyashi Maru exercise, and got a
commendation for original thinking. Broke the rules many times since
then, defied Starfleet orders on a regular basis, and was considered a
hero, because he - like others such as Picard to Archer before and
after him - was successful. Something that doesn't work in real life
much, does it?

I'm not saying there aren't times when they had to do so, because they
had information that their superiors didn't, or that there was no time
to get authorisation for whatever change of plans they had in mind.
But it seems to happen more than not; how can an organisation sustain
itself with such a seemingly casual disregard for the chain of
command?

I can think of only one episode where the hero is proven right for
following orders was in "The Wounded", where Picard stuck to Starfleet
orders and stopped Maxwell, even though Maxwell was right in his
assumptions about the Cardassians.

What does anyone else think?