Going back to the OP, the idea was to talk about the science of all this.
Here's another scenario: your buddy tells you that he spent last night listening to music on some kind of recorded media and it sounded great etc. and he invites you to come by and listen. Now if you have some good sound science that tells you that his recorded media will never be as accurate as some other format, what do you do, tell the dude that it's not worth it to go there? No, that would make you a bad buddy! So you take some stuff to consume that goes along with the music and enjoy it and have a fun time.
I guess sometimes when we get on these threads here and tell people that their CDs or their LPs or their flac files are not accurate enough, it sours up fast because it's not a positive vibe to introduce into the listening experience, man...
BUT... the OP was not doing that! He was openly sticking to the science!
Sooooo... if you're not bringing science into it, then you're the one raining on your fellow audiophile's parade. Said audiophile wanted to talk about the science of the thing.
There is a bit of an antiscience wave going 'round lately, usually voiced by people that, well, how to put it charitably, they didn't exactly ace their way through math and science class in high school...
btw Shannon's theorem is obviously correct and not to be questioned, since that process took place before it got to be called a theorem. So as far as upsampling is concerned, it's mostly a crock for listening although there may be some cute tricks for artificially enhancing the music during the production process that are available with higher frequency sampling (I wouldn't know about that). But for playback, 2N sampling rate yields resolution up to 1N frequency and that's just basic fourier theory.
The other aspect to this is the higher bit count leading to greater sound level resolution. If the noise floor on our audio devices is low enough, this can make a difference, but does that EVER happen? Do our homes have a 60-100db noise floor? None of mine ever have.
I went to the opera the other night and took the SPL meter along. The soprano on her solo arias was around 75 db (back rows of the Chandler). On a previous occasion I took the meter to the Disney, mid-hall (in x-y-z axes) and Mahler's 6th reached peaks in the low 90s and typically played around 75db. That tells me that in terms of loudness, I can probably get the same fidelity at home with 16 bits as I can get sitting at the Disney (as far as noise floors, etc.).
If the very same recording sounds quieter/deeper/etc. with 24 bits than with 16 bits then either your house has a noise floor ca. 100db or the people producing the 16 bit version did not get all they could out of the technology. With this answer I don't blow off what someone is certain that they have heard, and I don't blow off the hard work of math and science that has taken centuries to accumulate and, for some, mere seconds to blow off as inconvenient.