SPDIF to CDP vs direct CD playback sound difference


Recently I put together a Raspberry Pi network streamer for my father, who uses fancy speakers connected to Mark Levinson 390s CD player. According to him, although the sound quality is quite nice, it doesn't provide the full "sensation" of a sound coming from the direct CD playback when comparing a same track. I won't be home until a few days so I haven't had the chance to hear the difference myself.

For SPDIF output, I'm using Hifiberry DIGI+ PRO attatched to the top of Raspberry PI (ALSA, default config) and use Airplay (lossless) to stream TIDAL (lossless). Airplay volume is forced at 100% regardless of device volume.

I try to stay away from differences that I can't reasonably prove (because I'm broke) and I don't have the greatest ears either. That being said, I cannot understand how this particular audio chain can suffer such quality loss. Everything is digital until it hits the CDP, and I don't think there's a fault within its course. Hifiberry and toslink connection will add jitter for sure as it is not bit perfect, but it won't be anywhere close to being audible. One possibility is that the CD player is not handling digital input the same way as it reads a CD, but I doubt it.

Is there any hidden "gotcha"s I've missed?
snowmanp
It isn't clear how this is configured. First you say you're using SPDIF connection from the Digi+, but then you mention a Toslink connection, which is likely to be your weak link.
Oops, sorry for the confusion. It’s Toslink.

For some reason I thought they were the same.

Edit: so S/PDIF can be either toslink or coax
I cannot understand how this particular audio chain can suffer such quality loss. Everything is digital until it hits the CDP, and I don't think there's a fault within its course. 

Well, you’d be absolutely wrong.  I’m guessing you bought a cheap streamer and hooked it up to a computer that’s used for things other than audio.  If that’s the case it’s no wonder your father, who’s obviously more attuned to high-end audio, is less than thrilled with what he’s hearing.  The computer and streamer are riddled with cheap parts, noise, and timing errors.  It’s not as simple as just 1s and 0s, and everything matters in the audio chain.  BTW, are you using ripped CDs and/or a subscription streaming service?  That’s a whole other can of worms. 

Given the apparent quality of your father’s system and the level of sound he’s accustomed to, if you want him to really enjoy the streaming experience I’d recommend ponying up for something like an Innuos Zen Mk3 streamer/server that is purpose built to deliver high-end audio that will more impress and satisfy an audiophile like your father.  Yes it costs $2600, but what’s the point of spending less if your father doesn’t like it and likely won’t listen to it?  Just my $0.02 FWIW.  Best of luck. 

cheap streamer and hooked it up to a computer that’s used for things other than audio
Have you had any experiences with Hifiberry Digi+ Pro? Price doesn't equate to quality.

BTW, are you using ripped CDs and/or a subscription streaming service?

No idea what you're talking about either. Do you mean the high frequency digital imprints on streaming services? Or do you mean things like FLAC vs WAV?

If you have no rational advice other than to waste a whole lot of money on a overpriced device designed for "audiophiles", I think I picked the wrong forum.
I looked around the forums after posting the prior comment and realized that your reply isn't anything out of ordinary on this forum, considering that it is completely filled from bottom to top with people paying $3000 for a barely $300 worth of hardware for the privilege of abstracting away high school level of competence in technology. These aren't high end amplifiers with diminishing returns, they are digital outputs. I'm sure those systems sound "fine", just like any computer that outputs 99.9% bit perfect digital would. Sorry for intruding on your garden, and I'll show myself out.