The Orthodox view of Baptism is not shackeled by legalism or weird metaphysics - Sacraments are prayers, the highest prayers, in which visible signs witness to and act as means for the grace of redemption (remission of sins, and assimilation to the likeness of God.) Orthodox Sacraments are something the Orthodox Church does - they do not exist autonomously, related to Her only by accident or simple "lawfulness" when administered within Her.
If the Sacraments were to exist outside of the visible boundaries of the Church, that would mean that in some wise those persons are still parts of the Church, even if not in good standing or a disadvantageous position. But that such exists, would be known only to God for sure. The Church operates on what it does know - and as such, it can either receive all by Holy Baptism (which given what can be known, is normative), or judging by what can be known in terms of exsternals, can admit those heterodox/schismatics who have been baptized (or even baptized and ordained) with the right "forms" by a far more lenient means, with the understanding that whatever may be missing will be supplied by the Church.
Thus, hypothetically speaking, if it turns out that say, "Joe Roman Catholic" who becomes Orthodox had in fact really received the grace of Baptism when baptized by a Latin priest, the Orthodox Church is not guilty of sacrelige in Baptizing him, because it operated on the ostensible fact that he was baptized by someone who was not an Orthodox Priest, and not in a canonical manner. It's the same situation as when there is doubt about a Baptism in a solely Orthodox context - and before anyone says anything, the practice of "conditional sacraments" is a relatively late western phenomenon; that's why it isn't done that I'm aware of, and certainly wouldn't have been attempted in previous ages. After all, God doesn't need us to tell Him whether or not He will renew "Joe Roman Catholic" - He knows this. It's His grace, it's His work - the Church is simply acting as His hands, and His witness, humbly working in synergy with Him. The whole notion of a "conditional baptism" is rooted in the idea of created grace, and a way of understanding the Sacraments which Orthodoxy definately doesn't accept as Her own. The sin of re-Baptizing someone, the sacrelige, is not in that one can actually do this or come close to doing this, but involves the malice and direspect of the wills involved.
OTOH, if it turns out (God knows) that "Joe Roman Catholic" in fact received something far less when he was "baptized", but is received by economia, then the Church knows that the unseen grace of Baptism will be bestowed when he is Chrismated, or perhaps even more leniently (since the traditional Russian books allowed for this), repents, receives canonical absolution, and is given Holy Communion. In either case, grace is infused in the soul and God makes all well.
This is why, in a real sense, however much "what if" territory one wants to indulge, the right of the Church to excercise strictness or leniency in these matters rests on firm grounds. Beyond this, it becomes a pastoral issue, which must be discerned with wisdom and for correct reasons. However, fortunately for those coming to the Church, this is something which they will not be answerable for, however misguided the decision in this or that situation may be. Which is why in the end, I'd recommend that those coming to the Church who are troubled by these issues...
a) speak honestly and respectfully to their Priest about this.
b) do their best to accept what he concludes on this matter, or as is really the case, what his (and your) Bishop concludes (since the Priest is ultimatly not an autonomous figure, but ministers on behalf of and by the authority of his Bishop.)
I have my own personal views on this matter. Namely, I basically agree with ROCOR's rationale in their 1971 Ukaz on the topic of receiving converts. I also think that it makes little sense for a practice which was intended to help people avoid being scandalized and make it easier for them to come into the Church, to become a stumbling block in and of itself. But in the end, the wisdom or lack there of in the modern discipline, is something the pastors of the Church are responsible for, and they will be accountable for it. Thus, in that sense, so long as something heretical isn't being done (which must always be resisted, no matter who is doing it), we ought to do our best to be humble and accept the authority of our Bishop. For better or for worse, he's your man, until he either dies, clearly betrays the faith (and resists admonishment), or removed according to the canons and laws of his local Synod.