Component matching expertise - how do you do it?

I did not think that could be done, but excellent synopsis @ghdprentice . I fall into the musical category as well, so this made a lot of sense to me. 

@ghdprentice Nicely done! Thanks very much.

I'm not the expert that you mention, but I can tell you how I arrived at my current system. As @ghdprentice mentioned, I sought out components that I felt would satisfy my personal tastes.

I first selected my speakers based on prior experience with Von Schweikert.  I liked what I had, but I wanted a better version of them.  I spoke to Von Schweikert and they assured me that the Endeaver RE would be a big step up from my VR-4s.

I next looked for an amp.  As with my speakers, I liked my aging Coda amp, but wanted an improvement.  I consulted Doug Dale with Coda and he recommended the V1 version of the Continuum No 8 as a good pairing with my speakers.

Next came the preamp.  This time, I veered away from c-j and went with a Linear Tube Audio MicroZotl.  I spoke to owners of them and it appeared to have the aspects that I liked from c-j, but an improvement in other areas.

Some of it is luck, but I ended up with a system that I like.  I've tweaked things with different tubes, cables, etc.  

Nothing really scientific about my approach, but I ended up with something that I enjoy.

ghdprentice+1, it is also good to have mentor to teach you as simple as it can be. Listen to his system and ask questions. Robert Harley’s book is very helpful.

What you listen to, and the people you’re getting info from are certainly factors. I don’t consider myself an expert, but anyone’s subjective audio expertise is only as good as what they’ve been exposed to, and the info you get is only as good as the source.

A complicating factor is that there’s really no wrong way to build a system that you’re satisfied with. What we like is subjective. One of the things that catapulted my audio hobby was the opportunity to get well acquainted with audio gear that performed at a very high level, and was well above my pay grade. Otherwise I was stuck with reviews and what’s popular in the stores.

Determining what you like in a system is a big step, and that can change as we age and mature. Some people want thumping bass like the system in a dance club, some want high volume like a rock concert, others want their system to sound more like what they hear a symphony hall. I prefer the latter, and am a proponent of listening to a lot of natural acoustic instruments and voice so you’re well versed in what they should sound like, because it makes for a good reference.

Technical info is fine, and it’s great to have some basic understanding, but unless you’re designing audio equipment, or looking to measure you’re room, most measurements don’t really tell us much about how a combined system is going to sound.  It's good to gain some knowledge about room acoustics, because it's a huge factor in the sound you get.  Setup is critical.  Getting to that elusive system synergy is somewhat of an artform combined with dumb luck. Again, knowing what you like is useful.

One aspect of audio that I have learned with time, is that corporate greed is alive and well, and has an ever present influence on what’s available, what’s reviewed, and how things are built. The bigger companies seem most likely to be guided by shareholders and boards of directors. No harm in being a bit skeptical.

Get out there and hear as many systems as you can....join an audio club, go to audio shows, visit the dealers you have nearby. Flipping used audio gear is another possible way to get familiar with pieces of equipment in your home. Good gear that’s priced right should be worth what you paid if you opt to sell it. In the end, what YOU like is really the most important thing. It’s long journey for many of us. Enjoy!