There would be several such reasons. Not all of them I would be willing to discuss on a public forum. I do not wish my story is somehow used or taken to be an attempt to throw shade at the Orthodox Church. Nor do I wish my story be taken as in any way an encouragement to follow my lead out of the Orthodox Church. The reasons were serious, painful, and unavoidable. That is not to say it is the fault of the Orthodox Church alone though it was partly responsible, nor do I believe it was entirely my own sinfulness that caused my departure though it was certainly part of it. I left the OCA in good standing and my removal from the ranks of Orthodox clergy is entirely due to my leaving Orthodoxy. That's about as much as I am willing to say about it.
"Western Rite" would have caused me to stay longer, but ultimately it would not have been enough. Besides that I also do not think Western Rite is really what it seems. Though I am friends with Fr. Benedict Andersen (now a Roman Catholic & Benedictine monk) I am less well-disposed toward the BCP as he is in his thesis for Saint Vladimir's Seminary concerning the Rite of St. Tikhon. I concur with significant parts of his thought as therein expressed, but ultimately, I think there is nothing (or next to nothing) which has its sole origin in Cranmer that can be "baptized, redeemed, and used" in an Orthodox (or Catholic) sense. By that I mean that to me the BCP is structurally flawed and beyond saving. That said the Rite of St. Gregory - with the Epiclesis added - is also a dead end. The Gregorian Canon expresses a different, and older, theology as do Byzantine Anaphoras and the lack of an Epiclesis is a feature of this antiquity. The Gregorian Canon did not drop the Epiclesis ... it never had one is not supposed to have one. The addition of an Epiclesis is a severe distortion of the Canon. At least that is how I have come to look at it. Iow Western Rite would not have worked for me since, as I see it, it is adapted to fit a Byzantine development in doctrine not characteristic of the West.
Perhaps I could add that when you speak of "Holy" Orthodoxy, I have since discovered that this "holiness" is not exclusive to Orthodoxy. I would be quite comfortable speaking of "Holy Christianity" in which Orthodoxy participates, as does Catholicism (either Anglican or Roman), and I would not categorically wish to exclude Protestants either. Christianity is much more complex phenomenon than neatly fits in anyone's apologetical filing system.
Fr. Gregory Wassen