What types of difference in quality do you see? I'm not a chocolate connoisseur but it is interesting. I do pay premiums for coffee and cigars though. :)
Ingredients and care in the roast are the big things. You can taste the difference between chocolate made with cane sugar vs corn syrup, or in how much oils or coagulants are mixed with the cocoa butter. You can feel that same difference in the texture. The origin of the bean plays a big part as well, same as with coffee. Cacao beans bring in all sorts of fruity, earthy, and other flavor notes, which a good chocolate maker can turn up or down depending on how they tweak the roasting process. Also, good chocolate should be shiny, and snap when you bend it, a signal of a good grinding and tempering process. Compare this to Hershey bars (even their dark bars) which have a dull finish and either bend or crumble. Like with coffee or beer (or cigars, I assume), it takes time and effort to refine your palate for chocolate.
I’ll note that I had an eye-opening moment regarding the flavor of different beans at the Tcho chocolate tour on the Embarcadero.
At the end of the tour they do a tasting of bars made from single-origin beans. With the only additives being varying amounts of milk and sugar, one bar tasted bright and citrusy, another was earthy and nutty, and another was rich and (for lack of a better term) “chocolatey”.
It makes total sense in retrospect, but I’d never considered how much the flavor of beans by themselves can make such a difference.