Question

Regarding your article on Modern Orthodoxy, you raise the issue of using overarching considerations and also mention the matter of conversion. In addition, you quote Maimonides (specifically as an opposing position) as saying that someone who cannot refrain from speaking slander should go live in caves. So I just wanted to point out (and comment) that Maimonides דווקא strongly supports the meta-halakhic approach, even leniently.
In a responsum in Pe’er HaDor (section 132), Maimonides rules in practice that it is permitted to free a non-Jewish maidservant who had been living with a Jew, and likewise to convert her and marry her to a Jew, even though by doing so one is knowingly violating an explicit rule in the Mishnah (Yevamot 24b). Even so, Maimonides permitted this from the outset and not only after the fact. The explanation Maimonides gave for this is: “For the sake of the welfare of penitents, we said: better that he eat the gravy and not the fat itself, and we relied on their statement, ‘It is a time to act for the Lord; they have voided Your Torah.'” Not only that, but he even writes there that they should be married with blessings—that is, not with guilty feelings or anything of the sort. 

In other words, Jewish law does not allow a convert to come and say, “I am converting for the sake of marriage” (and Maimonides is the first halakhic decisor to innovate that the religious court must actually check this), and nevertheless, because of the need (or a meta-halakhic consideration), he permits it. He also notes that it is preferable that he eat the gravy and not the fat (as an instruction to the religious court itself, or to the rabbi who asked him the question), which is exactly the opposite of Rabbi Isaac Arama, who ruled that “they should eat the fat” as individuals, so long as the community does not “eat gravy” with official permission.