You might be surprised by hearing some very nice sounding DACs / players from long ago. They will absolutely measure like dog crap compared to modern. But our ear-brains do not process information via Fast Fourier Transform!
I tried an RME ADI-2 Pro "Black Edition" and hated it. Measures great. I hated the Benchmark DAC-1 too, back 20 years ago when that was all the rage - great measurements for its time, and was being dubbed "best DAC at any price" etc. Have a 30 year old Meridian 566 DAC. A real dinosaur. Very rich, warm, vibrant and natural tonality. Musical. More like my vinyl playback, in these aspects. Not as refined nor detailed as great vinyl, or modern digital. But probably more enjoyable (to me) than most modern digital. I had a R2R DAC too (Yggdrasil) and it didn’t have this quality, at all.
The technical progression of DACs over the past fews decades, from a mathematical and engineering standpoint, has been immense. But when metered as enjoyable listening devices - the progression has been far from linear, and not always in the "right" direction. There have been gems and dogs in every era.