I would have to say yes. I know there's a lot of discussion that higher end pipes are all about aesthetics and the grain, so let me tell you about my pipe evolution.
The early years (pre 18)
I smoked mainly cigars and corn cobs with whatever tobacco I could steal from my uncles without them noticing. I absolutely detest cobs for this reason probably.
College days
I had a few pipes all relatively cheap. I wish I could remember the brands, but by cheap, I mean cheap. These pipes smoked hot. Still a big jump from cobs, but I knew that there had to be better pipes. Some of them may be KWs which may account for my distaste for these, that and the fact that all wrinkled old men I knew smoked these.
Early Work Days
My pipes were 20-30 bucks. Back then I was buying Bjarnes Vikings for this price, and these pipes were pretty good. Compared to crap I smoked in my early days, I was in heaven. I had trouble spending too much for pipes due to being alone in the world and survival being my ultimate goal.
A Little Later in my Early Work Days
I had given up the pipe for cigars. Didn't have one in my place. Then I got married, and my ex wife expressed an interest in pipes. So we bought another of these Bjarnes (this is the oldest pipe I still own) which were now costing a little more than the 20 and 30 that I remembered. At this point, I realized that I enjoyed the pipe once again, and picked up a few to make a quick rotation.
My mid twenties
I was making a little more money and bought my first Peterson. Oh Boy was I in Heaven! I told myself I'd never smoke cheap pipes again (please note that I had spend 70, the most I had ever spent on a pipe in a local shop). I fell for the sales pitch of the "Big Three" and bought many Peterson's and Savinellis.
Fast Forward to about 3 or 4 years ago...
I was still smoking my Petes and Savis (1 or 2 Stanwellls that just didn't smoke right for me). Then something happened.... I discovered Ebay, and I was also just making decent money and stepped up to pipes that were about 100 to 150 bucks. Now let me elaborate, with each step in grade (and price), I found a pipe that smoked alot better. I was now smoking some Dunhills, a Castello, I mean high end pipes that I had gotten on ebay for good deal.
THen....
I had purchased a Tinsky Corral on sale about Christmas maybe 3 years ago. It was a bulldog and is owned by a buddy from another forum now. I could not believed how much better this pipe smoked than just about anything I owned. It was on par to the Dunhills and Castellos I was smoking. Then the boss tells me I'm getting an 800 buck Christmas bonus, and I immediately bought 5 more Tinskys.
The last 3 years
I got my first high end Rad Davis. Great Horny Toads! I started looking at other artisan pipes, now spending at least 300 per pipe and not regretting a cent.
Epilogue
Ok, my impressions, many will say that a good smoker is a good smoker no matter what it costs, and I will say they are right to a degree. But the stars have to align just right, you have to throw some toad eyelashes and light some incense while chanting a Haittan nursery rhyme. When I buy a Tinsky, rad Davis, Ruthenberg, that pipe smokes well from the first light. not begging it to build cake so it doesnt make hair grow on my tongue...
Some will chime in and say that I am just paying for pretty grain. But have y'all smoked a Roush, let's say? I mean, I'm not sure these pipes would win a beauty contest, but the two I have are some of the top smokers in my collection. Cool, dry, just fine smokers. I'm sure there are reasons for it; I know Larry cures or ages (whatever it's called) briar that is already quality wood. Artisans such as the ones I mentioned will not sell a bad pipe nor use a bad piece of briar. There's no flaws to disguise, nor poorly aged (cured?) briar used by others.