I'm trying to find some sort of free tool - probably an external application - that'll let me just click buttons on the keyboard or on-screen to play a variety of chords, like the keys on a chord organ. Doesn't even have to be MIDI, but if it can be hooked up to CbBL and used to trigger MIDI notes, that's even better.
I'm trying to out of break out of my C-major-based keys playing and get my ears primed to creating stuff that I wouldn't usually expect - especially since I'm producing a bit of lo-fi hip-hop and neo-soul lately, so I want to try out some more subversive, less poppy progressions.
 
I reeeeally feel like something like this is out there but multiple google searches didn't really bring anything... anybody know of something that matches what I'm looking for?

I don't know of any free ones, but I have several of the inexpensive options. Are you willing to spend any money?

Komplete Kontrol software from Native Instruments will do this, anyone could get it fo free at one time, I do not know if this is still the case.

It will drive a VSTi in the software, inside a DAW or stand alone. In a DAW it can also output MIDI so you can record your MIDI chords to a new MIDI track.

https://www.codefn42.com/chordz/

This is free, then you can donate. It's deceptively flexible, with some tricks up it's sleeve.
https://www.kvraudio.com/...rds-by-insert-piz-here

 

Insert Piz Here did some great work in the past, but the dev(s) have disappeared. Their website has been suspended.
 
If one of their apps does what you want, great! At least they are 64-bit.

Ahh that's a shame. When you delve into midichords, you find it as tricks up it's sleeve like assignable midi out. Never tried it, but should be able to play 1 note on he keboard, and create a four part harmony route to four seperate midi voices, such as Baritone, trombone, tenor and trumpet.
 
 

Kamikaze
Ahh that's a shame. When you delve into midichords, you find it as tricks up it's sleeve like assignable midi out. Never tried it, but should be able to play 1 note on he keboard, and create a four part harmony route to four seperate midi voices, such as Baritone, trombone, tenor and trumpet.

At least you can still download all of their MIDI apps from KVR. Good on them!
 
Like I said, if one works works for you? Awesome!

Fabulous!!!! I haven't had a chance to test any of these plugins but I'll aim to do it today or tomorrow.
Thanks a lot, guys!

Cthulhu has a chords module for playing chords with one finger.  Cthulhu can generate sounds, or it can route MIDI to another synth plugin.
 
Demo available, purchase for $39.
 
https://xferrecords.com/products/cthulhu
 
Cthulhu VST/AU Demonstration
https://www.youtube.com/watch?time_continue=107&v=3t2yD1kX2_w