Regarding being raised Catholic vs. being a convert -- I said I was going to mention an insight I'd been chewing on, and then Amber sidetracked me into the last post, which led to some good comments (thanks commenters).
Just a day or two ago I came across B16's commentary, in Jesus of Nazareth, on the parable of the two brothers, aka the parable of the prodigal son (Luke 15). I had always read the two brothers first as the story-on-its-face, and also as representing the pagan world and faithful Israel. Indeed B16 discusses this common and traditional interpretation. But he also goes on to describe another angle:
...[W]hat Jesus says about the older brother is aimed not simply at Israel...but at the specific temptation of the righteous, of those who are "en regle," at rights with God... In this connection, Grelot puts emphasis on the sentence "I never disobeyed one of your commandments." For them, more than anything else God is Law; they see themselves in a juridical relationship with God and in that relationship they are at rights with him. But God is greater: They need to convert from the Law-God to the greater God, the God of Love. This will not mean giving up their obedience, but rather that this obedience will flow from deeper wellsprings and will therefore be bigger, more open, and purer, but above all more humble.
Let us add a further aspect that has already been touched upon: Their bitterness toward God's goodness reveals an inward bitterness regarding their own obedience, a bitterness that indicates the limitations of this obedience... There is an unspoken envy of what others have been able to get away with. They have not gone through the pilgrimage that purified the younger brother... They actually carry their freedom as if it were slavery and they have not matured to real sonship. They, too, are still in need of a path; they can find it if they simply admit that God is right and accept his feast as their own. In this parable, then, the Father through Christ is addressing us, the ones who never left home, encouraging us too to convert truly and to find joy in our faith. (pp. 210-211)
It's kind of cliche (and almost new-agey sounding) to write that everybody needs to find their own way, but here is Benedict coming right out and saying it: They, too, are still in need of a path. Everybody needs to make a journey of conversion. Without that, living the righteous life is just a bunch of rules that somebody else foisted on you because you happened to be born into one family and not into another. And it's pretty discouraging when you find out that following the rules doesn't always get you where you think it ought to get you in this life.
Benedict points out that the elder brother's response is not given to us. It's left open whether he stomped off angrily, refusing to have anything to do with such an unfair dad, or whether he accepted the father's generosity and joined in the rejoicing. Maybe he went off to try out being prodigal himself.
But at least it gives me a model to think of the position that the "cradle Catholics" that are my children might be in.