What makes one pipe better than another?

You hit it! The quality of the fit and finish, the quality and treatment of the briar in many cases, and the marque.
If you are talking the quality of the smoke as opposed to the quality of the pipe, there are a few other considerations. Number one, for me, would be the personal preference of the smoker, the experience of the smoker is certainly a consideration also. Personal prejudices should affect how a smoker thinks of or perceives the pipe's smoking quality. The tobacco blends used, a smoker's frame of mind, the feel of the pipe in the fist, esthetics, etc, all combine to define, in a smoker's mind, how well a pipe smokes. It's pretty subjective.
Also, I'm guessing expectations would weigh greatly in an evaluation. Someone who doesn't like a particular brand will most likely, or very infrequently, ever "experience" a great smoke from a pipe of the "detested" brand. If you anticipate a poor quality smoke, you'll most likely get one.

I've seen prices range from $5 for a cob to several hundred for a nice briar.

Click to expand...

Try several thousand. The price of some hunks of briar will boggle your mind!
Here's my take on what makes one pipe better than another, regardless of price. Comfort and smokability. I like the pipe to feel good in the hand, and I like the stem to feel comfortable in the mouth. In most cases, the stem by any maker is going to be somewhat comfortable, however some makers put more emphasis on this than others. I had a couple pipes early on that I know now, the stems were awful. I like a decent draw. I don't want to feel like I'm popping my eyeballs out sucking on an extremely thick milk shake, regardless of how loosely I packed my pipe. Of course, I like a pipe to be something nice to look at too. I'm a sucker for nice grain, and can hold a pipe and just look at it, appreciating the grain and the shape of the pipe. But cost doesn't always make or break how well a pipe will smoke. One of my pipes cost brand new about 50 or 60 dollars but is one my best smokers and I enjoy it as much as some of my more costly pipes.

What makes one pipe better than another are a variety of factors, fit and finish, quality of materials used, the perception of the smoker, the technique of the smoker. From a purely utilitarian standpoint, a $5 cob will serve as well as a fine briar costing 100 times that amount. They will both do a decent job of delivering a pleasant smoke, provided the smoker has got down the basics of smoking a pipe.
Higher end briars offer other pleasures than mere utilitarianism. There are the myriad esthetic choices in shapes, woods, graining and staining, the comfort of a well designed and executed hand carved stem and bit. To some smokers those elements are as important as the chamber/airway drilling and as such, makes the pipe better than a pipe of more modest manufacture. That $5000 pipe might not smoke any better than a $5 cob, but the pleasure that its craftsmanship provides to its owner makes that pipe a better pipe. Conversely, for someone more focused on tobaccos and getting the most flavor without being bound up by esthetics, etc, the $5 cob might be seen as better.

You should figure out a budget you'd like to work with and shop around. There are, as you stated, a dizzying array of offerings at any price level. Though I do have a few mid range Savinellis, Stanwells, and Petersons, some of my 'best' pipes are of unknown make and cost me under $30 (unsmoked estate pipes). They smoke cool and dry, and look fantastic in my opinion. I'm not one to get too caught up in fancy bands, stems, or 'artisan' pipes but that's just me.

Ive smoked a few pipes and have yet to understand what a "good smoker" is. They all smoke like a bowl with a hole and a mouthpiece. I've never smoked a "bad" pipe. All this talk still confuses the hell out of me.

To me a bad pipe has a very uncomfortable button , smokes hot and or wet , regardless of technique.
Rarely I have run into a pipe that just plain tastes bad.

sablebrush52 said it all, +1

There are all kinds of things people talk about that makes a good pipe.
But here is what they ALL mean when it comes down to it if you like it, its a good pipe.

I think that everyone hit the nail on the head. Kudos all around, great responses. Or, maybe I've just been on this forum for too long, ha ha. Or my senility is kicking in... more so... Oh yeh, cats.

In addition to what's already been said I have to say that for me a lot has also to do with how open the airway is. I prefer a more open airway. Easier sipping.

Uneek, I've modified a lot of my pipes. Especially the ones I picked up earlier in my smoking hobby. And, even on a few more recent ones that I really fell in love with the looks. Nothing wrong with that in my opinion. I'll even give the button a little fine tuning to fit my preferences.

+1 Nate.
While this forum CAN be a wealth of information, don't let it be an albatross around your neck. Smoking a pipe is much simpler than people take or make it to be. Also consider the source of your advice, just because someone has the time and willingness...
I asked a similar question...http://pipesmagazine.com/forums/topic/is-it-a-good-smoker
...and received the same useless? information.

If you want to see chaos and uselessness, got to a bicycle forum and ask what makes a good bike. I am pretty sure that 98% of the participants there are under 16 years old, but they have no qualm in name calling, making everything political, religious, good, evil... And to even ask whether anyone there considers the skill and fitness of the rider might be more important than weight, gears, and tires, you get pounded and pounded by kawabunga flip haired gear heads. Ha ha. This is what I love about pipes. I think that most of us realize that the skill of the smoker can compensate, making it so that someone can make a beater into a great smoker with packing, cadence, and really getting to know how a certain pipe wants to be smoked. If you smoke like a frieght train driven by a meth head, you'll burn out even the top end of Dunhill or a Becker.
A few weeks ago, Skip at The Briary gave me an estate WDC that d a cracked shank that he was going to toss. I banded it, and fired it up, and it smoked itself for me. It was one of those moments where a I felt like every pipe I have owned prepared me for this one pipe. The stain is mottled, the rim chipped, and it's not a style pipe that I would ever buy, but it has given me many moments of sublime smoking pleasure. Someone else may think it not so great a smoker, but sometimes a person's personal skill lines up with the attributes of a pipe.

I don't believe that there is one perfect pipe that we could all agree on, because we have all developed different styles and skill of smoking. So, it's a very opened ended question with no one real answer, IMO. But, I'm not very smart.

@Cosmic
Exactly...

It all comes down to price, if you paid up the ass for it, in your head it will be a great smoker.

You have to look at them like your favorite pair of jeans, it is the pipe you pick up the most, with out you realizing what you have in your hand, heck if you hang out with a group of friends, sometime they will now what kind of pipe you always have around.