Justin,
When I found your post this morning, I was taken aback, quite surprised actually. As I've thought (and perhaps said) before, you and I are probably more similar than different.
If there has been a landing strip of grace in the whole Dormition Skete affair (at least for me, though I suspect it's been this way for some other folks as well), it's been a stern lesson - how not to think, how not to be. I'm not refering to any particular idea, so much has how one harbours their collected knowledge.
As strange as it may sound, there is a way of being "correct" all the while ending up absolutely in the wrong. In my own case (I will not pretend to speak for others) it was the realization that I had forgotten my first love, what presumably would be the first love of anyone professing to be a "Christian" of any sort.
So called "strict" ecclessiological positions, while having a symetry and logic to them which is very appealing (though I think if one delves even deeper you'll eventually find problems in this...but that search wasn't immediate for me, it took realizing the following first before I even bothered with this), pose one big problem: they create a noose in which no one will be justified, even those who profess them, not a single one. This includes the position OOD espouses; this even includes those "strictest of the strict", the "Matthewites". Only at the price of entertaining double standards ("forgive us our debts, as we forgive our debtors"), can one escape this.
But the even bigger "revelation" is that not only do the contemporary "zealots" have the footing cut from beneath themselves, but worse yet, so do our immediate ancestors in Christ - even those who lived well before the contemporary problems which now assail the Orthodox world.
Recent discussions here and (more so) on the Paradosis list involving those still loyal to Archbishop Gregory, embody precisely what I mean. Besides being utterly bereft of even simple human kindness and civility, we are now being told that basically the Russian Orthodox Church has been anti-canonical and crypto-ecumenistic in it's attitude and practice (in receiving converts) toward various western heterodox bodies for centuries (though not with the consequence of actually "undoing" the Russian Church in centuries past...we cannot admit this I suppose, because Gregory's validity depends upon it not being so!). Apparently the likes of St.Elizabeth (the nun and royal martyr) are only counted as Orthodox Saints in the same way we would count catechumen-martyrs as members of Christ - since according to the "correct" logic of the D.S. crowd, she died "unbaptized", save in her own blood! Suffice it to say, this is now the understanding of the Russian Orthodox Church which has canonized her, but why be troubled with such details when we have 20th century men to interpret the sacred patrimony for us with no reference to it's own outlook and assumptions?
While perhaps the D.S. crowd embody this problem unto absurdity, I don't think their error is unique to them: theirs is an extremism in measure, and not in kind...quantity, not quality.
Seraphim