According to your subjective experience is it better to upsample to DSD (256/512) or PCM (max frequency allowed by DAC) ?
Subjectively, DSD256/512. Please note it is entirely possible my subjective experience is affected by having seen measurements.
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I think it depends on the topology of the DAC, the rest of your kit, room and your own ears/brain… Some can be objectively measured and some not…
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As @Ddude003 alludes… Not all DAC’s are created equal in this regard… Some are PCM-centric where there is no unfettered 1-bit signal path to a simple output circuit provided, where the 1-bit PDM (DSD) signal is converted to multi-bit PCM… Others are DSD-centric, providing a pure 1-bit PDM signal path to simple low-pass output circuitry.
Subjectively… It is up to you to make that sound-quality assessment… 
… Just keep in mind that the design-bias of the DAC will have great influence on the final subjective audition (Among other playback influences)
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As there is a very nice upsampling system used within Audirvana, r8brain, it only costs you a bit of your time to try it out for yourself, on your DAC, kit, room and ear/brain…
If you are using speakers in your room this is where the most influence on sound usually occurs and it is measurable…
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Equally influential as the speaker/room synergy, if not more influential, is one’s subjective level of listening skills (Active vs Passive) among other cognitive bias and hearing acuity, that will have a direct influence on one’s ability to discern contextual harmonic, dynamic and spatial elements imbued in any given recording, in any given playback scenario, at any level of acoustic neutrality.
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@Agoldnear, I would appreciate it if you would allow the OP to grok what I am suggesting/alluding to without your spin on it… If he/she gets it then great and if not well another missed adventure into audio nirvana… Klaatu barada nikto…
Removed the references… 
Not intended to steal your fire.
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I want you to know that you are an amazing resource here supporting the Audirvana community and I appreciate all you do!!! We are both fire starters… 
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I appreciate the sentiment… I value your insights and support as well, we are all plus’d by your experienced insights… Thank You! 
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