There is a very interesting study from MIT. They studied why steel being as hard as it is can be dulled by shaving soft hair.
A new study by MIT engineers shows how shaving can damage blades. Human hair, 50 times softer than steel, can chip away a razor’s edge, the engineers found.
news.mit.edu
The consensus was that "simulations explain how heterogeneity in a material can increase the stress on that material, so that a crack can grow, even though the stress is imposed by a soft material like hair". -Tasan
In order to make longer lasting blades: "The basic idea is to reduce this heterogeneity, while we keep the high hardness." -Roscioli
In that article we Can see priceless animations shot with SEM technology that showcase the mechanics of cutting hair.
So your Theory is pretty much spot on. The only problem is: what to do with stubborn low laying hair? Those are pretty much impossible to cut perpendicular in relation to the centerline of the hair shaft. And the answer - while seemingly obvious - to stretch the skin (stand Up the hair), imposes another Challenge. As you said, we need to stretch only to the point where the hair is not Falling under the skin level after being cut.
Well as I mentioned many times, my hair crawls over the skin rather than grows out perpendicular to skin. So if I don't stretch, I don't cut perpendicular to the hairshaft's centerline. If I do stretch in order cut perpendicular, I cut below skin level.
So exactly as you said, I began experimenting with my technique again, to perfect it even further. All the mentioned factors play a role and need to be performed in harmony, then I need to "reprogram" my muscle memory to make the art of shaving more convenient and improve further.
So in my last shave I did not raise my chin up to stretch the skin on my neck, but rather pushed it down. To create a smooth surface for the razor, I only gently pushed/pulled with my free hand fingertips. I added an extra, Across the grain, pass. It was a little uncomfortable, unorthodox and awkward. Even though it was incosistent in terms of how even the closeness was, some places were BBS. I ended Up with mild razor burn, but it cleared up and there are no ingrowns forming yet. The skin Has more redness in comparison to the electric shaver. But it is overall a result with which I am generally pleased. On the first try!
I will keep pursuing this new approch, experimenting with aim to create the least pointy end possible on my hairs.