Measurements are mostly diagnostic. 99% of DACs are such that 99% of people can't tell the difference between them, regardless of how they measure. Measuring equipment are orders of magnitude more sensitive than human ears. Headphones and speakers themselves have orders of magnitude more distortion than your DAC or AMP. Old-school R-2R DACs (like your Gumby) has not and still do not measure nearly as cleanly as Delta-sigma DACs. However, many careful listeners who care about both sound and measurement, such as
Stereophile, attest they sound more "organic" or "natural".
Translating what is measured to what is audible is something quite difficult. Some things, such as distortion, noise levels, channel imbalance, etc. are audible if they're severe enough. This level of audible severity are orderds of magnitude higher than what would look tolerable on measurement devices.
Ultimately the question of what sounds good isn't very much related to measurement. There are subtle differences in the way difference source equipment sounds, and holistic distortion as a sum of measured and unmeasured parts come together to form a unit's sound. Sound distorted in certain ways can very well sound better, wider, deeper, better imaged, whatever-word-you-want-to-use than completely undistorted sound. This is why the entire industry of DSPs exist, as an extreme example.
So who knows. Maybe some equipment combinations add something subtle back into the sound of certain tracks that was lost during recording & mastering, resulting in a holistically more organic/natural sound. Maybe some tracks sound worse and others sound better. It's all just dancing at that point.
But we do know less jitter is better than more jitter. We do know less THD is better than higher THD. We can say "this unit measures better." That doesn't mean it sounds better.