> I honestly believe this is one of the most end-user unfriendly decisions in the digital music world.
Eeeh, you're brushing past A LOT of decisions across the years, many much more unfriendly than "Lets dump undocumented but plain-text XML into a file and change the file-extension". At least some engineer as Ableton thought enough of us to let it be plain-text, that's pretty friendly compared to all the horribleness out there.
> That requires clicking around in Ableton though, right? My goal is to generate like 100 different projects and jam on the effortlessly.
Yeah, if you just wanna send midi out to one channel, I think you'd be able to do it with 2 or 3 clicks or something like that, unless you setup a template and you'll only have to do that once.
Do you really have that many unique midi setups you switch frequently between? I have one "template" per setup, that I made once, that is used for a starting point for every project, where each one has a slightly different midi/audio in/out setup. But when I wanna jam, I essentially open up the template, then save-as, and it's ready for midi in/out and audio in/out, maybe something like that could work for you?
Basically, instead of trying to aim to generate all combinations up-front, have one template as a starting point, go from there when needed.