This reminds me of a conversation I had some years ago with a collector of ultra high grade Danish pipes, Nordh, Ivarsson, Chonowitsch, etc. These are pipes that sell for between $3,000 and $18,000. I asked him if a $10,000 pipe smoked noticeably better than any others and his response was, "They smoke about as well as my Grabows".
When you say high end pipe, what does that mean in terms of a cash outlay? You you mean $100, or $1,000, or maybe $10,000, like you pay for a Joura King or some obscenely overpriced Dunhill? Or are you talking about maybe $400 to $600 for a mid price range artisan made pipe by a respected maker? Or $100+ for a decently made factory pipe?
As has been said above, the "smoking experience" is a very subjective phrase. And as has also been said above, spending more enables you to buy a better made product, more care taken with materials and assembly, possibly a thinner, and hopefully, more comfortable bit. For a lot of smokers, the "bite zone" significantly impacts their enjoyment of their pipes.
But if you are only speaking about basic mechanics, a $10,000 high grade isn't going to smoke 100 times better than a $100 pipe.
On the other hand, if you're really into status symbols, smoking a $10,000 pipe might give you a woodie that a MM cob doesn't. Pleasure is very subjective.
If you want to potentially get the most bang for the buck, check out estate pipes. They offer a significant reduction in price and access to some of the best pipes made.
Please keep this in mind. Pipe smoking is 75% technique and 25% equipment. If you haven't worked out the basics of this not terribly difficult pastime, a high end pipe isn't going to do much for you.
Last thought. In today's environment, I'd be focused on buying more of my favorite blends to cellar, over buying an expensive pipe.