When do you really know if a wine is good - or not? Next morning...
This thread tells more about all the posters, than it says about wine or music... mcslipp (good post, sir) mentioned humility... less the person actually knows how little they really know, more arrogant (and ignorant) they are.
If we drink long enough, and if we are open to taste all the different wines we have available, we could become more informed. Or, more entrenched in what we prefer - or what we think we do. All in all, that too is a very personal thing.
In my opinion, HiFi equipment is a tool. No more, no less. If I must, I can compare HiFi equipment to a glass, used to taste the wine (or Cognac, or Armagnac, etc). One can have the best HiFi setup money can possibly buy, but if a recording is crap, all you going to hear will be that crap. No stereo can make mp3 sound like live event. Suddenly, measurements are not important any more. Same for Wine or Cognac. If your VS is a headache in the bottle, the best tulip glass will not prevent that hungover... Guess what - some XO are not much better!
And if you can't make yourself buy and try $100 bottle of wine, stick to the beer. Life is too short and wine is not for you. Better yet, just drink water.