will
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I seem to recall us having some different experiences in the past about FLAC versus uncompressed files. In all my tests back in the day, using the "best" ripping software for Mac at the time, I heard a difference. The Flac was good seeming, but more focussed, less complex and nuanced... big deals to me, and the more refined/complex info from uncompressed rips implying more complete rips. And since drives were getting pretty cheap, and my listening collection was maybe 500 disks, I went with uncompressed files. Might be worth some tests.
Also, everything matters as your experiments indicate, but as things get better overall, weak links that were not noticeable can become so.... so cables that once were better without comparison, or vibration mitigation, or anything, all can make a difference, so it may be time to play with these things again.
Another thing I found back when, was that a Macbook Pro running on its battery, sounded less good than a Mac Mini, using the same OS, the same player software with the same filter tuning, and the same system adjustments for audio. A sensible theory I heard is that though the Macbook Pro was using good parts to make it small, fast and light, and Mac being into good (quiet) parts in general... so it would seem to be quieter by comparison to many. And a Mini is similar in need for good parts to make it small and powerful, but the MacBook has a screen, and this is a noise maker, and the Mini is made of an aluminum block with all its noise and vibration benefits.
My setup was really revealing though. As illustration, I used (and still do use) firewire for my cyro'd drive enclosure, using a drive tested to sound good by trusted friends. Presumably the chips and electronic matter, and why not. But where I was going, the firewire was good because I was using a USB DAC, so on a different computer buss than the DAC. And a little weird to me then, but not surprising now, I could hear subtle differences between normal firewire cables, enough for choices. And using the one I liked best, I could choose one direction over the other for a little better sound. Not giant, but a choice.
Also, in my systems, the player software is bigtime. All the big players I have used with Mac sound good, but they are definitely different and have different tuning tools, which can mean a lot to me... so it could be worth some play also.
And not least, when my buddy worked with a guy to develop a seriously tuned version of Mac OS Mavericks, it was a more streamlined OS version to start with. But after removing something like 200,000 lines of code not necessary for audio, by concept, and by sound, it really was a notable difference... smoother, more solid, more harmonic complexity and spacial information, more everything really. So all the work folks are doing to create simple systems can have merit in terms of sound... just depends on how good the ears and systems and goals for presentation are.
All that said, I have been wondering about the Holo Red, which I think has a streamlined Pi 4 OS, and is designed by a brilliant guy who also listens while making exceptional tech. I am no expert by any means on this piece, just glancing around so far, but it could be worth a look. It has been some months, but I think I recall early reports being quite good, and if I am not mistaken, I think it does net streaming, disk streaming, and Digital to digital conversion. Don't believe me without checking, but what comes to mind. Might be able to basically "trade" it for your Denefrips converter???
Some thoughts anyway, and good luck!
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