The idea that our circumstances of birth are reflected in the horoscope is an interesting one, although I think that looking to our ascendants might not be the most descriptive place to look.
The moment at which we are born is encapsulated in the entire horoscope, and while our circumstances of birth might be gleaned from the nativity, these circumstances would probably show up in the mother's chart with greater prevalence, so we ought to compare our own horoscopes with our mother's, where we are lucky enough to know her birth-time.
The tenth house is the mother, so what would looking here reveal as to the circumstances of birth?
In my own chart, the ascendant comes from a sextile of Uranus, and onto a square of Jupiter in Scorpio. My birth by emergency caesarian might be reflected in the aspect of Uranus to the ascendant, but to expect every emegency caesarian birth to have such an aspect would be quite a tall order, and I'm reluctant to knock my ascendant back a few degree's to make it fit the bill, especially in that I take the 'transpersonals' with a pinch of salt anyway, and I question the extent of their influence in natal astrology.
Jupiter in Scorpio, which is about to square the ascendant, actually rules the tenth cusp, and so is a significator of the mother, and perhaps this upcoming square reflects tension between my mother and I, given the circumstances of my birth?
Looking to the tenth cusp, I have Venus in Virgo, closely about to square midheaven. Venus being a natural significator of the mother, particularly in a diurnal chart such as my own, and the aspect being a tense one between Venus and the 'mother' cusp, might have some relevance.
Virgo is a 'non-fruitive' sign, and my caesarian was necessary because it seemed I was very reluctant to come out into the world.
Having said all this, I'm probably reading far too much into it.
I'm not sure you can tell the circumstances of a person's birth from exploring the ascendant or nativity as a whole, but if you can I would like to know how. I think it is more probable to find relevant symbolism of unnatural or complicated births when looking at the mother's chart also.