Bambu:
You have it backwards. Chalking properly is an outgrowth of being a better player, not a prerequisite to it. Sure, the "slung down low like a heavy metal bass player" Corey Deuel "shake-drilling" method works to get chalk on the tip. That's not the question. The question is, as a serious student of the game, is one observant of the wear and tear on their equipment? Does that person observe other accomplished players, keep an open mind, and try these other methods?
As a player gets more and more accomplished, they also become more and more of a student of the game. They learn what are the "right" and "wrong" ways to do things, try them (even the "wrong" methods -- sometimes you can learn something here, too), and adopt what works best -- both in terms of performance, as well as wear and tear, and finally, aesthetics. Let's face it, the chalk wipers look more "technically correct" than the chalk drillers, wear and tear on the chalk notwithstanding.
Personally, I learned to wipe the chalk (in an "X" pattern across the face of the chalk, catercorner) after being a chalk-driller for so many years. That was over 20 years ago. My chalk wears down evenly, with a noticeable "X" pattern/grooving, until it's 1/4-inch thick, at which point I finally retire it.
-Sean
