I think this is a common problem with very-difficult games that lack permadeath. The only real penalty they can hit you with is setting you back a bit, so the game really amounts to redoing the same territory over and over. This can work if the game is skill-based or designed to make that entertaining (IWBTG, Dark…

Jim Sterling is primarily a comedian. He can sometimes use that to highlight issues he feels are important, but taking him 100% seriously is like taking the old Steven Colbert seriously; it’s supposed to come across as self-deprecatingly over the top.

I think “content warnings” are a bit harder to mock, though, since the term is so blunt about what they really are.