A suggestion for a new piece of software, for the developers out there willing to get their hands dirty a bit.
(Since my developing skills are near zero, so eh....)
Basically, a music player that converts (any sort of tune) into a chiptune (in real-time?) and plays it. Various sound sets can be chosen -- from 8 bit ones, to 16 bit... super mario (snes) sound set, etc. Bonus points if its CLI, made using c++ code.
Here's an XKCD describing the development situation you just described.
Converting audio into a different set of tunes, especially if they have multiple layers, is ridiculously difficult. There already exists MIDI converters online a google away that can create chiptune-esque arrangements from input songs but they SUCK, doing nothing more than trying to match input frequency averages to the target frequency of every midi note. But just asking someone to create an app (let alone a free open source one) that could make a usable chip tune with the slightest awareness of its input tunes is a very very tall order and this is not the right community to be asking it.
Now. That said, if you just want to map input MIDI's or some other raw format describing the actual tones (not just an audio waveform)- that would be doable with a little table lookups.
Honestly... what I had in mind was a modern song (with vocals, etc) being converted in real-time through a "winamp-esque" music player (think: "Open file", then after the song is chosen, "Converting to chiptune, please wait..." then the song is played.). But since this is a stupidly difficult task... then sure, I'm okay with a "standard" midi-to-chiptune converter.
So I work in game audio. I have a masters in music composition, and beginner knowledge of coding just to add a few lines of audio-related code to my client's spaghetti code.
What you're asking for is not a simple task, and will certainly need AI or machine learning or something along those lines. You could more easily make something like this if its just a single melody with no other backing tracks (and there's plenty of software that does this), but to understand and distinguish separate instruments, including drums, hear them all as separate voices, and turn them into a whole other medium, is on a whole other stratosphere. If someone's going to make something like this, it's going to be made by a corporation and sold as a $1000 plugin.
But hey, at least it will most certainly be in C++, because that's the language of choice for most audio plugins.
Now I can't tell if I should feel stupid or like an asshole to request this. But eh... thanks for your highly-detailed (and professional) input.