Not exactly. I didn't spend ten years shaving ATG and then suddenly "figure it out." I spent ten years shaving WTG, occasionally using XTG on touchups, and rarely shaving ATG on my neck.
For a really long time I assumed I had sensitive skin. I don't, and the vast majority of people who think they do, don't either.
What I do have is an addiction to sharp blades. The one downside to really sharp DE blades is that they have a strong tendency to dive into the skin, especially when shaving against the grain. When you shave against the direction of hair growth, it pushes the hair follicle against the skin, causing the skin to bunch up there. If you are using a sharp blade, it will slice through that bunched up skin like it isn't even there. A smooth blade will ride up over the skin, giving you a less close shave, but a more comfortable one.
Remember, this is all happening at a near microscopic level. If you get bunches of pin prick weepers, that's what is happening.
Is it worth going with the grain for all passes? Maybe. It depends on you, your hair, your skin, your tools, and your techniques. We've just talked about how shaving against the grain can cause irritation. It also shaves closer than shaving with the grain.
So let's say you shave two passes with the grain, and one pass across the grain, plus touchups, for a total of 3 passes.
On another shave, you do one pass with the grain, and another pass against the grain, plus touchups, for a total of 2 passes.
You might find doing a two pass shave is more comfortable for your face than a three pass shave, even though the 3 pass shave would technically be the 'milder' of the two shaves. Savvy?
(Edit: this is also assuming that the shave results were roughly even between the two shaves).
Blade choice doesn't dictate our shave style, but it does influence it more than people realize and it is why the mantra of the wet shaver will always be "Technique Trumps Tools."
The cotton ball trick has been around since there were cotton balls. If I recall correctly, I've seen it referenced in old barber training manuals.
As for the swirly spots of hair growth, you might try blade buffing (moving the razor back and forth in small increments) with a thin, slick lather, while following the spiral in the direction of hair growth, and then avoid shaving that spot in subsequent passes.
As for shaving pre- or post-coffee, it's almost always post-coffee, especially when I'm working. I'm a boilermaker by trade, so shaving is usually done after my post work shower in the afternoon. When I do shave in the mornings, after a pot of coffee, as I have been doing lately, I find the self vibrating razor effect doesn't negatively affect the shave.
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