This is a topic that I've been thinking about for a long time. I could make a start fleshing out my thoughts now, I guess.
The question is, since in addition to providing academic formation, Our Lady Seat of Wisdom Academy provides 'holistic Christian formation,' what does this mean? We are not a religious order; we are laymen. Our students are here for something else - but what exactly?
At the low-end of the scale this means positive Christian example, without any mandatory obligations of a religious nature.
At the high-end it means an extensive number of obligations, regarding prayer life, mass attendance, etc.
Determined by Expectations
What is right and what is wrong is not so much the question as it is what is the best given these circumstances. The circumstances are that we have a group of about 20-year olds, who are preparing for adult life. The expectation is that we will give them a good liberal arts education that will give them the best shot in whatever place they end up. They also expect that this will be done in a Christian manner, and that what they learn will be true, barring human error. This includes orthodoxy in theology.
Those things are probably universal expectations. Where students may differ among themselves (and the faculty and staff differ among themselves too!) would be over regulations respecting discipline, in what precisely orthodoxy consists, and over what ought to be mandatory, community practices (essential for salvation?).
The Present Condition
We have rules concerning dress code: no immodest dress, an interpretation with which I am in full agreement, I must say. Dresses passed the knees, no shorts, no muscle shirts, etc. And rules concerning 'nice dress,' which means no sneakers or jeans to class, basically, and collared shirts for the men.
We have rules governing 'inter-visitation,' which are more controversial. Some parents think we should not have any at all; some students think that our current arrangement is way too restrictive. Our arrangement is pretty good. I can't remember the exact current arrangement, but it's basically just weekends, after lunchtime.
There are very few mandatory religious things: community mass and supper every Monday evening, one day of recollection in the Fall, prayer at the beginning and end of each class. That's basically it. Now, of course, if one mandatory mass makes sense given our cirucmstances, it is not foolish to ask, why not more, or, is even this a legitimate impingement of personal freedom?
No one worth debating with would question the legitimacy of rules concerning the use of bad language, etc., but what about the religious character of our formation? Is it intrinsically perfect? What about mandatory attendance at a daily rosary or daily mass? When I was in the seminary daily mass was mandatory, as was attendance at morning/evening prayer. The whole question is not easily handled with the retort that this is a college while that is a seminary. What is it about the latter that makes daily mass indisputably correct, and what about the former than makes once a week so obviously correct? I think the thinking behind this once-a-week mass is that it's generally not a great idea to mandate the sacraments, but that there is no reason why we cannot get together once a week and pray as a community the Church's prayer (i.e. the mass). Prayer and force do not mix well, though, and the powers-that-be recognize that.
Virtue and Rules
Neither, really, do virtue and force. Yet creating a positive space through regulations regarding external conduct (dress code, language) is not simply, or even primarily, about my personal virtue; it's about my obligation not to scandalize and not to impinge upon other people's freedom to live in the manner they expected they would be able to live at this Catholic college.
OLSWA is small enough for the idea of 'community' to work at a very practical level. Community at Steubenville, for instance, would function quite differently - the whole school could not be present in any given place and time, especially not at mass. We want to keep OLSWA small enough to ensure, amongst other things, that this type of community that we presently enjoy be maintained.
In a community like this there could be a temptation to enforce a path of sanctity that, while this path is good in itself, fails to recognize that virtue must be presented with choices. Parents, teachers, etc. must ensure a good environment so that choosing the good will be possible and attractive, but for a young adult it must be a choice. Sooner or later it will be. A student must be able to look at his or her whole life and range of options and decide within that the best way to life out one's spiritual life. The problem with the seminary was that once the young fellows left its secure corridoors their rythm of prayer so very often fell apart. One must be given the opportunity to see the good itself, and adjust one's way of life accordingly, not simply respond to a set of regulations, even when the individual recognizes them as objectively or theoretically good.
Thus, OLSWA's minimalism is to be recommended. But of course, it is not minimalistic compared to most other places. Our primary responsibility is to provide a safe, pure environment in which Christian teaching can be implanted and grow up strong. In a few weeks we are planning on having a day of fasting for the material needs of the school. Can you imagine mandating fasting?