Largest challenge nowadays is just getting someone to use it.
I've run a server for the past few years, and I plan to continue for the foreseeable future. And of all the things that lead to an issue, its just getting someone to not immediately throw their hands in the air and flop around. It's not hard, and I'm fully willing to help those people, yet for some reason, it never sticks.
I don't even know if a lot of people these days can grasp/enjoy the concept. I don't know of any popular social media that just throws you into a community of people that don't know, except for Discord, which still has a way different feel.
It's strange, and there isn't much I would say I could do personally. But I'll keep my server going as long as I physically can, out of stubbornness if not anything else.