I first started to play many years ago (well before CtC), and I never gave much thought to just how/where the pick smashes into a string. In recent years, however, I would think on-and-off about a Rusty Cooly quote where he hits the top half of the string (and doesn’t go deeper). Eventually, I concluded that with a reasonably pointy pick like a Dunlop Flow 2.0mm (the random size that I chose), one can start to feel details of the pick impact on the string; I was ignoring this before. However, when I try smoother tips (like the classic Fender shape), it seems harder—but not impossible—to get an idea of depth. I note a rigid pick makes measurement easier.
Therefore, a hypothesis: Some people use picks with a point (Jazz III, etc.) because they want to feel the pick/string interaction and thereby control the depth of the pick’s impact. I’m still relatively new to this (a few weeks?), but it seems really eye-opening, I would regularly hit with too much pick. This also reminded me of an old product,