Modesty, manners, and the like

First: an intro summary to a series of essays about the virtuous dimensions (or lack thereof) of modest character.

Second: the essays.

Some questions that arose while reading these:

At what point does modesty and/or the expectation of it become an overly repressive force?

Insofar as modesty and restrictive temperament are to be valued as 'good', or 'positive' traits, should any outward display that particularly lacks these traits, i.e., displays that are rather not-so-modest and in your face, be relegated to the realm of satire as the most reasonably appropriate venue in which to let it all go. For example, FUCK YOU, YOU MOTHERFUCKING PIECE OF SHIT! is a rather immodest statement. This approach could work well in winning people over... in a Monty Python film (though I admittedly don't recall this line being uttered in any MP films that I've seen). And of course, if a lack of modesty can only be appreciated in satire, then to what degree should the satire be taken into account as reasonable or constructive?. . . after all, it's satire (I should note that I personally believe satire has it's place in effective and constructive communication-- I'm just noting the strange idea that work of a satirical nature often tends to carry more intellectual weight than cut and dry facts organized neatly onto a spreadsheet.)

That said, should anyone expect others to take them seriously-- and expect to proceed with positive and/or productive results-- with anything other than a modest approach? In what cases could an immodest approach, other than in works of satire, be a more effective, or neccesary means of communicating ideas?