> Why does taste have to cost hundreds and thousands of dollars?

Because part of the point of "taste" is to exclude others, or, if you prefer, to distinguish oneself (which is the same as excluding others). Money helps reduce the uncommitted.

Because it's completely subjective and thusly has no hard value, it's literally the same problem as pricing art. Consequently, you may as well charge 500-5000% markup.

Hmm, I thought that was the point. If that identical pair of boots were available at 19.99 no one would want them. (only slightly kidding)