The difference between D sharp and E flat

Anyone that works with me knows that I am a nerd about...everything. But especially note spelling. Sharps vs flats, etc. And I always come off as pedantic or as an asshole. Usually the latter. For me it's simple:

1) Is it correct spelling in the context of the harmony/key? (The key is E major. No, that is NOT an A flat minor chord.)
2) Does the note choice facilitate easier reading melodically? (Reading C sharp to E flat kinda sucks.)
3) Some combination/give-and-take of 1 and 2.

But that's not always enough. These are not heard examples. Those cases are fine on paper, but what about sound? Who cares if we call a D sharp a D sharp or an E flat?

Tonight I heard a great example. It's actually a great, familiar example of a number of things. And it helps that the verses and chorus are the same harmonically.

Radiohead, "Creep"

This song has two classic pop/rock harmony cliches:

-a major three chord (III) that moves to IV
-a IV chord that becomes minor (iv)

And here's where I can talk a bit about the difference between D sharp and E flat. The guitar plays different broken arpeggios of the following:

The chromatic line D, D#, E, Eb, is quite plain. And even out of context that makes sense: the non-diatonic note is spelled with a sharp ascending, flat descending.

But for nerdy/pedantic/asshole purposes that is not enough. Context is most important. In the key of G major, a chord built on the third scale degree is B major. Obviously. And a chord built on the fourth scale degree with a flatted third is C minor. Yes. Ok.

But beyond that...what is the difference between a D sharp as part of a B chord and an E flat as part of a C chord?

It's possible that not everyone hears this the way I do, and maybe it seems really obvious, but...man, I hesitate to say this word...the psychological effect of the D sharp is so very different from the E flat. I find this terribly profound. In equal temperament, these two pitch classes are the same. Yet within the contexts of B major and C minor triads, they mean such different things.

Just listen to the song, and listen carefully for that chromatic line. It's the harmonic and emotional backbone. Doesn't the D sharp sound bright? It "lifts." While the E flat is so dark. It really pulls down to the D, which is part of the G chord.

Again, maybe it's obvious. I know it's all mind tricks. Centuries of cultural conditioning. But still.

Am I over-talking this point? Eh. But I find it so interesting. And it's all tied to note spelling and context. So there. I may be pedantic AND an asshole. But sometimes I'm right.