I can give you an example from my experience. I got annoyed by my dull knives, so at first I went and bought really expensive knives, the ones made of hardened high-carbon steel that start rusting if you look at them dirtily. And I spent hours reading reviews before buying them. That's probably the "most expensive cup of coffee" stage.
Then I stumbled upon a Youtube channel that explained how to sharpen knives properly. So I bought $70 worth of diamond sharpening stones and re-sharpened my old IKEA knives. And they started working almost as well as my set of ultra-expensive knives, but they are far more practical. The expensive knife set is now a display piece in my kitchen.
Another revelation for me was that past a certain point, there's really not that much difference in the quality of sushi. It's just rice and sliced fish. Sure, there are individual variations between chefs in rice-to-fish ratio, maybe some special soy sauce here and there, but these are all just matters of personal taste. So I now just enjoy sushi for its taste. And instead of a looking for reservations in expensive restaurants, I just drop by my local sushi place and just ask the chef to add a bit more wasabi to the rice.