Since my system has been built primarily through the purchase of used gear which I usually compare with another similar component in my system, I tend to change components when I see an opportunity to acquire a piece that I have wanted to compare to something I already own. This method has provided a great education in learning to discern differences among gear, and it has proven itself as a valuable learning tool regarding matching speakers/amps and preamps/amps.
This is how I buy preamps, amps, digital sources, and wire.
Speakers are another matter. I tend to hold on to speakers longer because they're a hassle to buy and sell. IMO.
This is how I buy preamps, amps, digital sources, and wire.
Speakers are another matter. I tend to hold on to speakers longer because they're a hassle to buy and sell. IMO.

