I am not obsessed with cholocate, but a couple of times per year my mom and I will buy a pound of homemade chocolate candies made by a local woman whom we know that makes chocolates around holidays for a small list of loyal customers. There ain't no website / e-store / Facebook page. She sends out an email to about 15 people a few weeks before the holiday and either you want 'em or you don't. In addition to traditional candies, she sells holiday offerings like Santas, Valentines, bunnies, etc. The chocolate candies are clearly superior to the local and chain chocolate stores and a relative bargain: $16/pound. We usually order a mix of dark buttercreams and dark cherries - both are incredible.
In addition, maybe once a year I'll buy a really nice bar of extra dark chocolate, either from the chocolate section at Whole Foods or from a high-end chocolate store. I like trying different bars, but you can't go wrong with the Chocolove bars. I'll nibble on one of those over the course of a couple of weeks.
Finally, I am occasionally tempted to get a Whatchamacallit, which was my favorite candy bar growing up. It's never as good as I remember (the chocolate quality isn't good), but the overall taste is still pretty good within the "hot mess" candy bar genre. If some fancy chocolatier made a high-end dark chocolate Whatchamacallit dupe, I'd be in heaven.
Sarah