A lot has been seen and it is always fun to look at this thread.
My short answer to the original question “Do Expensive Pipes Really Smoke Better?” is that it cannot be answered as the definition of what constitutes a better smoke is different from person to person and even if we agree on some parameters of evaluation the subjective graduation of them would be difficult to have any kind of consistency.
I would instead reformulate the question in this way: “What is the minimum amount of $ I should expect to pay for each one of the different type of pipes (briar, meerschaum, morta and so on) for having an acceptable smoke and what could I expect to gain if I spend more than that?”. This kind of question can be probably answered in a more subjective way as there are minimum costs in material and workmanship which need to be factored for having a decent smoking pipe. If someone is offering you a new briar or meerschaum for 5 $ you should expect there is some problem with it.
So to this type of question I would say you should budget 50 $ minimum for a briar pipe and 100-150 for a meerschaum or morta given the higher cost of their materials. Above that if you double or triple the budget you can have some improving in smoking quality, but not proportional to the increase in price, increased likelihood of not having issues (basically buying insurance in some way) and better cosmetic. Above that point that I would put at around 200$ for a briar and 300-400 $ for a meerschaum or morta you only buy the cosmetic but it is difficult the smoking by itself will improve too much, maybe a little bit for the briars.
By myself I prefer to buy close to the plateau of what I think I can expect in terms of improving smoking capabilities, to give an idea I got a Tom Spanu briar for 240$, a Baki Meerschaum for 315$ and a Il Duca morta for 425$, I love all of them, they are beautiful and all smoke very well with no issues. Could I have a similar quality smoke spending half of what I paid? Possibly but it would not have been guaranteed and the aesthetic could not have been so good (which for me is important, for others no). Could I have a better smoke spending double of what I spent? If anything at that price tag probably it would have been marginal with the difference being mainly cosmetic.
At the very end everyone has to decide what are the important things they are looking in a pipe and then I would suggest to go for the best they can afford in that category. So for example if you like corncob it is perfectly fine, I would just suggest to spend 10 $ for a Meerschaum corncob than 1$ for a chinese cob, most likely you will be satisfied from the Meerschaum one.