I try to have a setup that is capable of doing bit perfect through all of the digital steps. Bit perfect from the music file, through the media player, through the audio drivers, and to the audio interface. I want it to be capable of doing that bit perfect. But when I listen I do things like enable a digital EQ or a software based crossfeed and at that point the bit perfectness ends.
Any processing that alters the bits in the media player is going to end the bit perfectness. That includes EQ, digital volume adjustment, software based headphone crossfeed, resampling, dithering, and other software effects. As long as I'm bit perfect up to that point I consider it good.
One case though where you want to be able to do bit perfect through from beginning to end is sending HDCD encoded music to a HDCD capable DAC. If you rip a HDCD to lossless, send it bit perfect through your media player and bit perfect to a HDCD capable DAC the DAC will be able to detect and decode the HDCD. If the bit perfectness is broken along the way the DAC won't see HDCD data and will play it as normal audio rather than HDCD decoded audio.