Help me - am I stupid

1) Upsampling helps by lessening the need for steep filters (for CD quality, filtering out everything over 22050Hz), it can also help reduce jitter depending on the implementation. Many DACs do this natively, so I wouldn’t do it on your own.

2) You can’t know what the original master track was done at, but it really shouldn’t matter. However, there are instances of sites selling copies higher than the master is in.

3) No, ~100kHz is the limit for peak performance for a DAC, Benchmark actually downconverts 192kHz files in order to get better performance (you can’t hear above 20kHz anyway so you won’t notice the difference).

That being said, and I’ve argued with a few people hear, DSD has no benefits that I know of and there is no need to go higher than 44100Hz as most DACs upsample themselves and better ones deal with intersample overs. And unless you have a dead (heavily treated) space, there is no benefit to listening to 24Bit, especially if we are talking 16Bit that has been dithered and noise-shaped.  

For fun, try and see if you can tell 16Bit apart from 8Bit with music playing. Now, that’s to show that music can do well in masking a high noise floor, but that’s not to say you can’t tell the difference between 16Bit and 8Bit when music isn’t playing, check this out, you can clearly hear that 8Bit is much worse, the site also lets you hear what dithering and noise-shaping does (keep in mind it’s demoing it for 8Bit).

@lohanimal

The auditory recall for humans is about 10sec, so hearing “benefits” over time does not exist, what people generally hear is simple the nuances in the music they missed before, which is why people suggest demoing with songs who know like the back of your hand, it’s also why the headphone burn-in myth exists. If I played the same track 5 times for a group of people and told them I changed something, it’s bound to happen that someone will say they heard a difference.

The only possible benefit (see caveat in below paragraph) for higher than 44.1 is if your DACs digital filter does not perform well enough to filter out the audio above Nyquist, even though even “cheap” DACs usually don’t alter anything below 19kHz.

However, due to how MQA works, if your DAC is MQA compatible and it doesn’t use different filters for the format, then there may be some benefit to going 96kHz. If you look at the Mytek Liberty’s response with 44.1kHz (for a reference to a good response, see the Chord Qutest), you see higher aliasing occurring, which may drive your speakers into distorting (same probability with vinyl), depending on how well the tweeter handles high frequency (as well as your pre-amp and amp).

I see no benefit to MQA over lossless PCM, any seeing how most DACs that support MQA also degrades PCM performance (which is one reason why some people may hear a difference going from PCM to MQA on the same DAC), I choose not to get a DAC that supports MQA.

By analog you mean vinyl? If so, CD has far better dynamic range and accuracy, it only loses to vinyl in terms of ultra-sonics (but I guess you can then say vinyl loses to 16/96 to 24/96 in that same regard), which while you can’t hear may cause the tweeters to distort.

There are no nuances that CD misses, 44.1kHz by proven by Nyquist-Shannon captures the 0Hz to 22050Hz range with 100% accuracy, not even 0.0000000...0001% loss.

I know some people who prefer the static of FM radio over the clean sound of CD, so while vinyl isn’t that poor, maybe it’s a similar thing for you.