The organoleptic analysis is almost an exact science: tons of chemical compounds create complex scents, flavors and textures that we can recognize with our senses. You can be good at it, you can train yourself if you are not, but, usually, there is a general agreement on the qualities of a wine. That doesn't mean that a good (or an excellent) wine is good to everyone. And this is the first problem. The second problem is that a recipe is a complex artifact by itself. If you add the complexity of a wine, the result is experienced differently by different people.
The biggest disappointments I had in my life were mostly when I chose the recommended wines with a dish or a menu: either I didn't like the wine or I didn't enjoy the pairing.
When I host a tasting dinner I try to pair 2 to 3 wines for a single dish so we can compare the wines and decide what we like the most. Surprisingly, almost everybody agrees on which one is the best wine but no consensus is found on the best pairing.