I like to listen to everything, all genres regardless of recording quality.
So I assess by randomly queuing up tracks to get a random sample of how things sounds overall.
Every recording is recorded differently, so I listen to make sure I can hear what is going on in each clearly, for better or for worse, and take note of the variations and unique aspects of each recording
Then I just listen to whatever I want to. If I hear a problem anywhere, I take note and address it, if needed.
Another benefit of using a random sample is that one is better able to determine when a particular sonic deficiency is common across multiple recordings (most likely a system problem) or not. If not, then sonic deficiencies can be attributed properly to the recording rather than the playback system