I did the emoji thing and even though I went through it correctly it did not proceed reliably.

Oh. That's not how it's supposed to be. I self-host my own (Synapse) matrix server. So I wouldn't know if there are issues with the network or something like that with the established, big servers.

several keys all associated with the same account [...] (And did the keys each also have another password too?)

Yeah, That's too many details. It should be: you sign up for a new account, keys are generated and you are requested to back up your master key. Maybe that backup can be protected with an additional password, I don't really know. From that point cross signing and all cryptography should kick in automatically. Everything should be handled without the user needing to worry about additional keys. And in my oppinion the additional inner workings should be hidden from the user. At that point you're set and once you log in with a different device or add a friend, a popup should open telling you to verify the other user/device with the emojis.

If everyone is bouncing around clients it’s a mess.

That is the most annoying thing with Matrix. I've also had this happen. Some time ago I had clients not support emoji verification. Or I try to write a bot in python and it runs on a server with no means of displaying emojis. I think Matrix isn't strict enough to handle the diversity of clients. In theory diversity is a good thing, but for Matrix... I've also had some issues with that exact thing.

[...] struggle collectively. I do not really think we get freedom one by one.

That is especially true for messengers and social media. There is the network effect. A platform has little to no benefit if it doesn't connect people and it's just you ;-)

Philosophically it’s kind of regressive to say that lost autonomy is deserved by people who fail to learn to the standards you think are reasonable in the areas you think they should know about. There is way too many things in the world we can’t all know about all of them.

I agree. I have compared this to the Age of Enlightenment before. There is some basis we need to agree on. Everyone has to agree they want freedom and be ready to put in some work and face the struggles. But not everyone needs to become a computer expert and have this as their primary hobby. Just being a follower should be alright, the only thing is you can't be annoyed by change and experiencing a dry spell every now and then. I think this is consensus and also how it works with parts of the FLOSS ecosystem. There are clubs and individuals who operate the servers and handle all the difficult and tedious parts of hosting. Not everybody can, or wants to do this. As a user it is your obligation to know how to operate your computer and smartphone. But it shouldn't be overly complex. That takes away from the spirit and makes it inaccessible for some people. And we want the opposite of that, spread the freedom amongst everyone who is willing to participate.

I really don't know what to recommend to you. Don't resign and let the technical difficulties keep you from getting what you want. It's the right choice. Maybe you find something better than Matrix for your use-case. I'm kind of in another situation, so my experience doesn't necessarily apply to your situation. Maybe have one person do the work, try out a few servers and Apps/clients and pave the way for the rest of the group. It definitely doesn't work if it's an uncoordinated effort and there are sub-optimal choices and traps out there. And it will scare some people off (rightfully) if they have to start over for the third time.

With our group, we have tested matrix for some months with two people, then a third and then a friend of mine invited all the other people. Most of them use matrix.org as their Homeserver. And we keep the room unencrypted for maximum compatibility. We don't give admin rights to everyone, that would lead to confusion. One person manages the room and they put in the effort to learn how to manage the room and help people get the app installed on their phones and join the room.