i will acknowledge that the recording medium makes a difference, but only on the very high end. i don't have a system like that and few people do. further, the reality is that the analog technology has an end of life. if you don't digitize it eventually, you lose it, and once it's digitized it should stay digitized. it makes no sense to dump it back to analog.
condition A: analog tape masters
this probably means a reel-to-reel and i want to be clear that my disdain for vinyl does not extend to analog master tapes themselves. this is arguably the highest quality recording possible, or was. but it degrades, even if you don't play it. you don't have to play the tapes from them to demagnetize.
in 2026, it is probably already too late for your reel-to-reel playback mechanism and it's probably well past the time to move on. it probably doesn't sound very good at all and you're probably deluding yourself, you're probably paying top dollar for a medium with no workable input source. you'd have to really, really, really like that one record from the 70s.
but, if something was recorded to high quality tape then it does continue to make sense in theory to master and manufacture it on high quality tape. these are not the little tape cartridges for your 90s ghettoblasters you had as kids. these are big, clunky reels. they are short in duration and it takes 20 minutes to swap them carefully. it costs like $100/lp. it's unworkable, but it's the best quality - in theory - for old analog masters.
in reality, then you need to find sufficient playback equipment, and you need to accept that the reels are probably warped and degraded and the result is it in truth probably sounds like absolute shit.
this then is best to worst - according to objective scientific analysis.
1. analog reel-to-reel, in theory. not in practice.
2. digital audio that was digitized from master tapes (as 24 bit), either as an optical disc or a file. same thing. note that you want to avoid streaming this to ensure clarity. download it instead. further, be careful about the effects of fans in computer equipment. netbooks tend to have less interference but bad sound cards. i use a raspberry pi with a dac for digital audio. another option is a dvd or bluray player with a usb port.
3. digital audio that was digitized from master tapes (as 16 bit) <---cd or download (flac). see above.
4. digital audio digitized from master tapes and compressed to 320 kbps mp3 is actually better quality than consumer analog media. it's actually less filtered.
5. commercial cassettes made from an analog master source (without digitizing) have higher frequency ranges than vinyl playback, in theory. in reality, your tapes from the 90s are probably so degraded that they're unplayable.
6. vinyl cut from analog is the worst available playback mechanism and on par with lossy digital audio formats, like 256 kbps or lower mp3, due to the filtering process
7. lossy digital audio
8. digital audio that was digitized from the for vinyl analog masters which were already heavily filtered is the worst possible choice. it's also one of the most popular choices, unfortunately.
condition B: digital masters
if you recorded to digital you shouldn't even consider converting it to analog. it's consequently the same hierarchy, with the analog playback sources removed.
however, upsampling doesn't increase quality. the quality has to be there in the master already. you get what you record at.
1. 24 bit digital (optical or digital, including lossless), if the recording was at that rate, legitimately, without conversion at any point of processing (very, very rare). really only relevant for classical music.
2. 16 bit digital audio (optical or digital, including lossless). this is the best you're going to get for 99.9% of non-classical music recordings in the commercial market.
3. 320kbps mp3s compressed from high quality ddd sources are better than vinyl because they have less frequency loss.
4. vinyl cut from lossless digital audio requires it to be mastered for vinyl, which requires hefty high and low cuts that the amplifier is supposed to rebuild, but it in truth can't do that without a severe decrease in detail on the high and low end. it just results in a bass blur and a treble ring. it's not only not comparable to any form of lossless digital audio, it's worse than a high quality mp3.
5. lossy digital audio (including almost all streaming).