I'm drawn to rusticated and sandblasted finishes, which tend to be more affordable than smooth finishes, so that helps keep things relatively affordable.
I've pipes from artisans and large manufacturers, and the difference in the quality of performance is negligible. At a certain point you're paying for aesthetics, which is fine. But I am not paying several hundred, or thousands, of dollars for a knot of wood I can hold in my hand. I'm not a craftsman, so I can't speak to the effort and talent necessary to make these high-end pipes, but Christ on a Wednesday, I can buy a quality shed or dinette set for the price of some of these pipes.
My bottom dollar is around $250ish for a pipe, maybe a little more if it really catches my eye. But any more than that is hard to justify personally.