Very well thought out responses, guys.
Setting up a system that allows you to enjoy reproduced music is, to my mind, a matter of assembling a system that pushes YOUR magic buttons. By magic buttons, I mean those qualities of music reproduction that make your ears and body respond positively to what you're hearing. To some, this may include tonal beauty and/or purity, lively portrayal of rhythm and snappy pacing, retrieval of recorded detail, protrayal of ambience and recorded space, holographic imaging, warmth, etc. - mix and match - everyone values something slightly different.
The task, of course, is to set up a system of components that maximizes the qualities of playback that YOU deem most important to you. Some components work very well together to achieve this - called system synergy, and some compontents do not work well together at all. Most of the time you'll try a set of components that sound pretty good together, but doesn't get it "just right."
That's why we're constantly playing with gear, right? Also because we think there's something more and better around the corner.
When I started out in this hobby, I didn't really know what did it for me. After a number of years listening to different gear and system, I think I pretty much know what I like. When I plan on buying a new piece of gear, I make a short list of equipment that's most likely to fulfill my needs and try to audition them, if possible. But you never really know how it will all work together as a system until you try it.
So it's a little bit like identifying your tastes through trial and error and experimentation over time. After you have an idea of what does it for you, the task becomes much more efficient.
At the end, you can reall enjoy your music!
Best,
KT