The wine analogy that Kirkus used might be the way to go here, but with wine the you can try many types easily and see what you like and have a collection of Cabernet, Pinot, Chardonnay, etc.
But with Hi-Fi, you can't collect to the same degree, and you cannot sample to the same degree. So I think for many people we rely on the audio equipment equivalent of the master sommelier, like reviews from Stereophile as stated above or sound engineers with a lot of experience and people who have been into it for a long time. The expense of audio, and the rate of audio collection, generate a reliance on expert advice in this kind of situation.
So what is the advice for the guy who started this thread, he likes his McIntosh gear. What would be an interesting flavor change, would a Plinius SA100 mkIII be an interesting taste choice? Better is pretty subjective, but how would a class A amp with his McIntosh pre be different?