A good pipe smokes great no matter what the price but I personally believe you'll have a better chance to get a better smoke out of a high end pipe simply because of the care that goes into it at all phases, including the maker hand picking the best briar at the mill.
That being said, it won't make a bad tobacco taste good. Some pipes smoke different blends better than others for different smokers. A lot of VA lovers prefer them in smaller pipes.
One thing you'll find is that your taste change over time. For years, I couldn't stand English tobaccos. Now I love them.