I don't know how much help this is, but here's my thoughts. Medium has been having a ton of server issues lately. For months. I wonder if newsletters aren't going out to save server resources.
Honestly, I wonder if it would be better to post them as stories instead of sending as newsletters at least until we see the 500 errors end.
But also? You could export your list and import it over at Substack. Then when you create the newsletter as a story, you can copy/paste it at Substack and it WILL get emailed to everyone.
Plus? Substack's "discover" feature will likely find you a bunch more readers, too.
P.S. And for what it's worth, I *would* actually enjoy seeing you dance to your odd French pop. But then, I loved Numa Numa, so there's that. lol