For some time I hated digital, and now feel that was because of how crude the early D->A conversions were. Maybe the recordings also had problems with jitter etc but the DAC was pretty crude and was the main weak spot.
Decades later we now seem to be entering a golden DAC era where the conversions are very nice and not requiring a big bank balance. In particular I’m looking at the Chinese LKS MH-DA004 which is being posted as even better than the SCHIIT YGGDRASIL. I have a used one on its way so should be able to judge for myself in a few weeks time.
But it can be a torturous path requiring something like a low jitter Auralic Aries as a bridge and, surprise surprise, digital cable quality can also be critical. I’ve only woken up to that this year so now use Canare F206 for the longer AES/BSU runs to the DAC. And I’m astounded at how much trouble and expense some people go to when using a USB connection to their DAC. The money would, IMHO, be far better spent on extracing a good AES/BSU signal.
And I should add I listen to the music via headphones, currently the rather nice Sennheiser HD800S. They can reproduce music far more convincingly than speakers and avoid room resonance problems. But yes, they are not so comfortable to use in hot weather and do take some time to get used to.