What are we asking when we ask whether things have gone too far?

The frum community is in crisis. A crisis of constantly questioning whether we are in crisis. My most vivid childhood memories consist of various authority figures questioning, discussing, or ranting about various activities that they viewed as having become trends, and the (potential) negativity of those trends. Our chasunas are too fancy, our music is too loud, our cars are too new, our wines are too old, our children are too overworked, or too lazy, our houses are too big, our yeshivas are too demanding or not demanding enough, we don’t have enough secular studies, or we have too much, we have too many conversations about stuff like this, or perhaps we don’t discuss these things enough.

In almost all such circumstances, opponents of the activity would concede that there is a justification some portion of the time, and proponents would concede that the activity is ill-advised some proportion of the time. It might even be fair to say, choosing one example, that a third of people would do well to lease a car, a third would be making a big mistake if they leased a car, and a third are in a gray area, and their choice will not have significant consequences.

In that light, what sort of scenario would need to present itself to warrant a communal discussion about the advisability of the activity? Alternatively, assuming people don’t *really* want to discourage the activity in all circumstances, and kind of concede that some proportion of people who engage in the activity do so justifiably, what is it that these discussers are actually trying to communicate or achieve?