Hi there.
I'll attach this picture showing this wingtip adelaide by Hiro Yanagimachi.
Pay attention to the brogueing along the sides of the laces. The lower end nearer the wingtips are markedly flared outwards.
This is totally a personal preference, aesthetic wise. It's just a look I'm not quite fond of. Because, to me, it throws the proportions off.
I just want to add though, that Hiro is a great maker and I have great respect for him. I'm just using the picture for illustration purposes.
As for the second question, if you are referring to the vertical "scoring" around the circumference of the upper part of the heel stack. I don't know if there is a specific term for it, maybe not. But it's just an aesthetic feature. Not difficult to do. They probably just run a tool, probably not dissimilar to a fudge wheel used on the welt, to make the markings. Most shoes have em. No stitching involved.
Thing is, this feature is not really evident in my pictures.
Do you mind circling the area that your question is directed at?
Sorry.