Why did you choose the components and speakers that are in your system?

I had Apogee Duetta IIs for years, loved the planar/ribbon sound.  I had to put them in storage for a while, and one got damaged while moving them back.  Long story short, I had a couple of DIY 2.5 way speakers based on Usher drivers I built that I used in the interim.  While they sound good, they didn't match the Apogees.  Did some speaker evaluations and wound up with Maggie 1.7i, being the closest within budget at the time.

Had a PS Audio 4.5 preamp, blew a channel shortly after hooking it up.  My old DB Systems preamp had a bad cap, and I wasn't sure at the time whether I wanted it fixed.  So I got an Emotiva XSP-1 Gen 2 preamp as a dealer demo.  I figured it was something half decent until I could make a decision on a permanent preamp, and at the price, I could probably get out of it even.  It served it's purpose.

A little while after this my Bryston 3B amp blew a channel.  Sold it off and bought a PS Audio S300 as an interim amp.  Good reviews and they offered to take the non working PS audio preamp on a trade with a generous trade in value.

Somewhere in there, I decided to get a dedicated phono preamp.  Thanks to many good reviews and advice gotten here on AG, I picked up a Herron VSPH-2A after talking to Keith.  It was more than I wanted to spend at the time, but any misgivings went away when I hooked it up and started listening.  Best move I could have made anywhere near the price point, I'm totally convinced of that.

Fast forward to a couple weeks ago, as a lark I put in a bid on a BAT VK-30SE preamp that I thought didn't have a chance of winning.  But it did :-).  Turns out it was just serviced (same month as the auction) by BAT and came with a brand new factory set of tubes to boot.

A side effect of the new preamp was that I appreciate how good the PS Audio S300 is.  I still want to eventually replace it, but I'm not in a rush at this point.  It's kept up really nicely with every change I've made in the system, and drives the maggies with authority at any volume level I would even consider for short periods, and does a great job on all types of music.  Pretty amazing for a real budget amp.

So, basically, some research, some educated guesses, a lot of listening, and some total luckouts. Good luck with your journey.  

I'm with oldhvymec, start with the speakers you like and build up to them.
I like ESL and Raal ribbons also.  AMT's are OK.  They all blend together satisfactorlly. They all require juice to perform so tiny amps are out.
And cooler is better for me since I do not own a power company or solar.

Good question!

You have to start with the thing you have least control over which is the room. I choose speakers likely to perform well in my specific room, then an amp capable of driving them very well, and things unfold from there.

I was an electrostatic and ribbon speaker fan for decades and spent most of my time and money trying to make them sound better... first massive power, then flesh out the sound to be more natural. But when I would make a change, one genera of music would sound better at the expense of all the others. Hearing details and bass seemed to be sonic goal. I listen to all sorts of music..

Then I got season tickets to the symphony about ten years ago. Completely unconsciously I radically changed directions and out of the blue (consciously out of the blue, subconsciously on purpose) bought some dynamic speakers (Sonus Faber Cremona) as a test set. I had heard these speakers while helping a friend pick out some audio equipment years earlier... I was struck by what I thought unique sound... not positively of negatively. Within a couple weeks I ordered some new ones of higher caliber. Then swapped equipment all to Tubed Audio Research Equipment. What happened was that with each upgrade my system got closer to real music instead of highlighting details or slam and each time all genera sounded better, not just one! My system got more and more musical... the details were still there but not highlighted so you would have to listen to the system and not the music. Now I am captivated by the music and not the system. You can see my system by clicking on my ID.

.
In retrospect what happened was I found an empirical ruler, the live acoustic symphony... instead of the current album I liked. In the past I would find test albums for reviewing possible new components for which I liked the sound. Through system component selection I would try to increase my enjoyment these CDs and to improving the obvious traits of the system (details, slam, low noise). But having the symphony as a standard, it turned me toward more musical... I can’t even begin to tell you how important a change this was. Suddenly not listening to the venue but becoming fully emotionally engaged by the music. I enjoyed the journey but if I could do it again I would have focused on lower powered, tube based systems with dynamic speakers from the beginning and had much more musical systems while getting to where I am today.