The only way to enjoy being an audiophile is to research, listen and understand, quite literally, the state of the art before moving cash around.
This sounds nice but doesn't have the benefit of being true. I don't need to "literally" understand a piece of gear, or its context, in order to appreciate it. For some it's the gear that's for sale; for others it's the sound of the gear. You seem to be describing the M.O. of those with the most acute disorder, not the cure. Needing to understand everything literally would ultimately confuse a person's decision-making.
Once you've built a system...just enjoy the music, it's not going to sound much different at a certain point.
But why "build a system" then? Just play music on your laptop. QED. Everyone will find his own balance; there's no one point of reference.