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The Church does not have an official teaching regarding exactly how Christ entered the world. It is certainly fair to say that Our Lady was not spared all pains of being a mother, she saw her only Son die in front of her. I'll take labor pains any day over that. She also, I believe, experienced pain if she stubbed her toe and such.

My concern is that such thoughts lead to the notion that childbearing is a punishment. I, for one, believe that Our Lady gave birth the same way most women do. Perhaps she had a heavenly c-section, but I don't think she did. Giving birth is such a powerful experience, it unites you with your child in such an intense way, I don't think God skipped that experience for her. I think her body worked with her Son's body to be born. It very well could have been painless, but to me, that's not the point.

Dignity is so much more than a physical state of being. I do believe that God did keep His Mother fully Virgin. But He was also like us in all things but sin and His mother was more than an incubator for nine months. If He wasn't born as us, then why the nine months? He could have been left on Mary's doorstep, still fully her child, since this is God we are talking about.
I have given birth twice, drug free I might add, and I just don't see the punishment of it. I don't think the words in Genesis referred to the actual giving birth pains, but rather the pains of worry, frustration and self-doubt that plague you as a parent. It's hard raising children to be the persons God created them and therein lies the suffering that was referred to in Genesis.

The Church does not have an official teaching regarding exactly how Christ entered the world.

Actually, it does. Fr. Geiger cites the Catechism of the Council of Trent in both his review and in his vlog. The specific reference is in Part I, Article II, under "Second Part of This Article: "Born of the Virgin Mary." Here's what it says:

But as the Conception [of Jesus] itself transcends the order of nature, so also the birth of our Lord presents to our contemplation nothing but what is divine.

Besides, what is admirable beyond the power of thoughts or words to express, He is born of His Mother without any diminution of her maternal virginity, just as He afterword's went forth from the sepulchre while it was closed and sealed, and entered the room in which His disciples were assembled, the doors being shut; or, not to depart from every-day examples, just as the rays of the sun can penetrate without breaking our injuring in the least the solid substance of glass, so after a like but more exalted manner did Jesus Christ come forth from His Mother's womb without injury to her maternal virginity. The immaculate and perpetual virginity forms, therefore, the just theme of our eulogy. Such was the work of the Holy Ghost, who at the Conception and birth of the Son so favored the Virgin Mother as to impart to her fecundity while preserving inviolate her perpetual virginity.