+1 with pretty much all of the above.
It's been said here that smoking satisfaction is 25% equipment and 75% technique. In other words, it's like sex.
But, it's also unlike sex in that fast and furious doesn't work for pipe smoking, ever.
Have you seen youtube videos where a great big burly bearded guy lights up his pipe and is sending great white clouds of smoke into the air around him and he continues to do so as he describes whatever point he's making?
That's the guy who doesn't know how to smoke a pipe. He does know how to cremate a pipe.
The only time that I puff on a pipe is during lighting. After the tobacco is burning, slow sips are the way to go. Curls of smoke, not great gushing clouds. Exhale the smoke through your nose. You get the most flavor from your tobacco when you don't superheat it. Smoking, like sex, is a pleasure best savored, not rushed through.
It took me a while to learn this, but letting your tobacco dry before packing can make a HUGE difference in the level of flavor that you experience when smoking. I find that most blends benefit from drying to the point that they feel dry to the touch, no sensation of moisture in that touch, but not so dry as to become crumbly. Dry, but still pliant. Crumbly crisp is too dry, and some flavor will be lost. Like sex, the proper amount of moisture is critical to maximizing pleasure.
Keeping your pipe clean and giving it time to air out between smokes is important and greatly benefits one's smoking pleasure. An overused pipe can go sour.
To cob or not to cob is up to you, but one benefit is that you get an inexpensive way to try different tobacco blends without having the ghost of one blend affecting the taste of another. And cobs make excellent smokers.
Smoking a pipe is not an endurance test, nor is it a stunt. There's no glory to be got from finishing the bowl without a relight. If the pipe goes out, it goes out and you relight. It's also not incumbent upon the smoker to thoroughly burn every last bit of tobacco in the bottom of the bowl. Doing so can actually cause harm to your pipe. If a load stops being pleasurable to smoke, dump it.
Packing varies on the type of tobacco and the cut. Experience teaches you the best way for you to enjoy a specific blend. It's not rocket science. Pipe smoking just takes a little practice, and a little bit of patience.
My experience regarding briar is that better grades have better, generally more uniform, capillary structure and possibly better endurance to stresses caused by use. How the briar is processed is more critical than how it is externally shaped. How the pipe is drilled, whether the draw feels effortless, is more important than external shaping.
Have fun. Don't take any of this too seriously.