As others have noted proper good quality fresh truffle is really worth it (unlike all the "it's no nicer than regular food but we've served it on a statue, covered it in gold leaf and sprinkled salt onto it off the top of a bald man's head" fancy food you can spend a fortune on.) Freshly shaved truffle is like if Willy Wonka decided to turn his hand to making the perfect savoury food experience. It smells like the most satisfying food ever and then the instant your teeth slightly penetrate the surface of the shaving it somehow seems to instantly fill every space in your head with that scent at double the intensity and your whole mouth is awash with a uniquly rich and warm flavour.
I love single origin chocolate and was once gifted a bar of Amedei Porcelana (sometimes called "the most expensive chocolate in the world.") It was, unsurprisingly, a perfectly executed bar of chocolate. Texture, balance of sugar to cocoa etc were all flawless. The flavour was delicate and perfectly balanced. It was like the most refined expression of the exact central archetype of what chocolate should taste like. I really enjoyed it and would recommend it to anyone who would like to experience the most perfectly chocolatey chocolate. Personally I found that while it was a flawless execution of a straight down the middle chocolate and I am very glad to have had it, I prefer a bit more character and so my favourite bar is still the Grenada Chocolate Co 71% (which slaps you in the face with big juicy tropical fruit flavour and is overall not quite as refined as Amedai Porcelana.) Though I've not had the chance to eat either in several years so I suppose it's possible they may have changed since...
If it costs over 60 euros or so, it's hard to believe it really is worth it. Maybe one time thing, but above that it really is a law of diminishing returns.
I think it probably makes more sense to relate it to the cost of something else rather than an actual dollar amount (as that will always change over time.) IE. If a meal out costs more than three visits or McDonald's or whatever it may be. FWIW, the Amendei Porcelana bars are about £12 and the Grenada co about half that.