listening to low quality

One of my musical passions is listening to live bootleg concert recordings, particularly Springsteen.

I haven't listened to any in quite sometime however, and have done quite a bit of upgrading since then.

I recently downloaded a recording of a show I saw of his this week, and listening on my computer's audio system, determined that this recording was one of the better ones I have heard. In fact so much so that a casual listener may not even realize this is bootleg made with high quality mics in the audience of a huge arena.

My computer audio setup is in fact better than many people's home stereo, using a tascam pro mixer's D/A, Audiocontrol cheap but good Balanced amps, and some high quality mini monitors that use use Aerogel mids (I have a seperate sub)

Listening on my main system however, (Atma Tube amps, PS Audio DAC, etc)
The recording totally falls apart. Hard to listen to. Not overly bright- but just thin, echo'ey, distorted, and not too enjoyable.

Back in my computer system all is well and I can really enjoy the music again.

I'm Just trying to think through what if any implications this has for my main system. It may make me think about those less than stellar real recordings in a new way.

After all ,it is musical enjoyment and fidelity to the original recording we're after, but can too much fidelity subtract from the musical enjoyment?

Just thinking out loud. Could something like a very tubey, bloomey, bufferstage that actually lowers resolution by a large amount and blurs musical details be a potential bandaid?

Anyone else use their megabuck gear to sometimes listen to recordings
that make the worst commercial recording sound like a Rudy Van Gelder in comparison?