The automatic tag closing behaviour is even specified now.
But look at it another way: imagine browsers accepted only valid HTML and every browser had some bugs in what they consider valid. Writing a document in a way that it displays at all might be a challenge already then. Add to that that not everyone is on the latest browser version (that was probably more true in the 90s as well) and you get all the current pains just with worse symptoms. I'm not really sure that's better.