study the guys who do this great. you will not be able to translate this 1:1 into 3d as the reference doesn't care about correct perspective from any angle. https://sketchfab.com/search?q=anime just searching anime on sketchfab gives you a ton of reference to check out :)
Yep, in theory, smoothing should average a perfect circle out of a square of ratio 1-1 but in practice, the more sides you have the more perfect the circle is, if you still go lowpoly-style you certainly want at least 6 sides, then 8, 12, 16... etc.
@FrankPolygon Hey mate thanks for the write up, it's really appreciated. I was a little confused as to the 1/6th segments when really it's 1/8th. The most difficult part is defining the stages between 1 and 2 you labeled. Once you commit to the angle/depths you can't really revert. Meaning you'd have to go all the way back…
@Thanez Thank you for taking the time. So far, the top-down thinking on how to approach this stuff hasn't solidified yet. I understand the solutions given to me, but as soon as I'm in any case that's not identical, I seem to be unable to apply the concepts. It's too bad there aren't more 1:1 tutors for this stuff!