Its hard to tell if the folks at Plex understand the position they're in. They definitely are dancing right up to the line of pushing people too far. I could see them trying to boil the frog with stuff like putting their garbage free streaming stuff front and center more. Like so there won't be one specific thing they do that makes everyone realize its time to leave.
I think one silver lining is that whenever it does reach a tipping point there's going to be a ton of support for projects like Jellyfin, so hopefully we see more feature parity - in particular for shared access for friends and family.