My equipment for listening to music in a way that I really enjoy is the following:
ancient iMac (iTunes with Sound Enhancer on the highest setting) > custom USB DAC (Burr-Brown Japan PCM2702) > Grado iGe3 earbuds
IMO the most important part is choosing good music to listen to! I don’t have any experience listening to audiophile-quality equipment that is more expensive, but I have played instruments and been around live music for 10 years and my setup is starting to approach a live sound.