I definitely second the motion on it being a branding problem. Stuff like sh.itjust.works seem to me like something that dark basement tech nerds would come up with that is "edgy" and really only used by them and other people like them.
I'm not really into the ironic "edgy" aesthetic and part of the struggle with this transition for me has been orienting myself in the space because I don't want to commit to some "sketchy" edgelord URL
Something interesting that Matt Mercer mentioned on their latest talkback was how often times he just creates problems but not a solution. Seems like a really great way to ensure the players are able to have freedom in how they approach things and you as a DM aren’t forced into ensuring a specific outcome