another short "pill" answer (i am on smartphone, will write something more detailed later, when i will be at my PC)...
comparing 16/44 and 24/96 might be pointless... because your digital hardware might be not good enough then the 24/96 playback is just flawed and with no meaningful sound quality differences compared to 16/44.
in fact, if you wish to make a proper comparison (like I did myself) is to individually compare both a 16/44 and a 24/96 capture directly with the analog source they were captured from.
it will be easier to hear which capture will sound closer to the analog source listened without any digital conversion involved.
Also, not any analog gear is good... there are so many cassette decks (but also so many amplifiers) where the signal passes through integrated circuits (the chips) which ruin the sound in a similar way as bad digital usually sounds... such analog audio gear will never do justice to a good analog source but it would still be good enough to listen to CDs.
Why I know it, about IC chips and such?
Well, it's many years I also work on audio gear... do consider that many good/upgraded transfers shared during these latest few years were transferred on some cassette decks I did restore and modify with my own hands to improve their sound quality (i.e. both my own and neonknight's RS-B565-MH).
comparing 16/44 and 24/96 might be pointless... because your digital hardware might be not good enough then the 24/96 playback is just flawed and with no meaningful sound quality differences compared to 16/44.
in fact, if you wish to make a proper comparison (like I did myself) is to individually compare both a 16/44 and a 24/96 capture directly with the analog source they were captured from.
it will be easier to hear which capture will sound closer to the analog source listened without any digital conversion involved.
Also, not any analog gear is good... there are so many cassette decks (but also so many amplifiers) where the signal passes through integrated circuits (the chips) which ruin the sound in a similar way as bad digital usually sounds... such analog audio gear will never do justice to a good analog source but it would still be good enough to listen to CDs.
Why I know it, about IC chips and such?
Well, it's many years I also work on audio gear... do consider that many good/upgraded transfers shared during these latest few years were transferred on some cassette decks I did restore and modify with my own hands to improve their sound quality (i.e. both my own and neonknight's RS-B565-MH).
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