I think you make some great points, Iconodule. As a former evangelical, the Western Rite was as foreign to me as anything Eastern. Although I'm sure you'll disagree, here are some further thoughts of Fr. Winfrey's that touch on this:
But I would question the statement that both rites are equally foreign. Everyone who has lived here in the West has heard Gregorian chant, and most everyone here is deeply moved by it spiritually. There are abundant hymns that are loved--even in the Protestant circles--that are cherished and fully Orthodox in content that are even used in the Latin tradition. The sense of anticipation following American Thanksgiving for Christmas is a cultural memory of Advent, which is uniquely Western. Fr. Alexander Schmemann said that only the Western Church developed a truly specific Nativity cycle. The cultural bias of westerners is to get right to the point, and that is one of the salient characteristics of the Latin liturgy. It follows the western mind. The eastern mind is quite different. It is lovely and authentic, but it is not ours as westerners. Regardless of one's subjective neutrality, one is the inheritor of the fuller western life that is found everywhere we turn and which was most beautifully expressed in the Latin Mass. That ought really not to be surprising, because the Mass is the highest point of man's experience and life and therefore it is the highest expression that is possible in any culture. What that culture has been formed by the historic, apostolic Church, then her worship is the pinnacle of our culture and all of our culture is ultimately carried in it. Culturally this is beyond anyone's subjective admirations or comfort.
I'm not posting this because I fully agree with him, but I find the topic of intersecting cultures and incarnational Christianity to be fascinating, and I think his comments bring up interesting points for us to think about. 
As another minimally liturgical ex-Protestant and while I would've found both the Western and Eastern rites to have been equally daunting and unfamiliar, the Western rites seem more "close" in terms of cultural heritage than the Eastern rites do. I'm not sure how to describe it myself, but I feel like I'm honestly ignoring a large part of my Western (Orthodox) heritage by immersing myself solely into the Eastern rite's life in all its forms.
Having gotten my bearings now, in a liturgical setting, I feel the same way (even though that setting is the Western Rite). I think that's what I find compelling about Fr. Winfrey's (albeit, sometimes
unclear) thoughts. There is something deep in my bones, by the sheer fact of me being a Westerner, that resonates with the Western Rite. My first Western Rite Mass was me balancing three different books in my hands trying to follow along, and I barely understood anything that was happening, but all I wanted to do was go back and experience it all over again. The chant, the vestments, the altar, the prayers, the gestures, all of it felt like I was remembering something I'd forgotten, even though I'd had no experience with liturgy at all.
As inquirers tend to do, I visited other Orthodox parishes, all Eastern Rite, and though I thought they were beautiful, it just wasn't the same for me. Some of what Fr. Winfrey says puts into words what I was experiencing, and what I think many (though certainly not all) Westerners have the potential of experiencing when the riches of the Western Rite are expressed and nurtured within an Orthodox context once again.
