Surely Italy won't find a way to fail to qualify again.
There's no way at all they will qualify from this group automatically if Norway beat Estonia, as I detailed. Surely the goal difference is far too much. Can you see the Italians putting 10 past Moldova and 7 past Israel? That's what they need to do, and hope Norway struggle to beat Estonia, and even then italy needs a handsome win in the last game against the Norwegians.
Their only real hope of automatic qualification is Norway not beating Estonia. The goal difference of Norway is too much of an advantage.
The play-offs are very down to luck. It's amazing to say but we could see Italy fail to qualify for a third consecutive time.
In a way they had the worst of both worlds - they tried to qualify for the NL Finals and failed (which isn't even an important tournament) and due to that they were playing catch up already in this group as Norway played 2 games before Italy played one. Norway were on 6 points with goal difference of +7 when Italy travelled to Norway for their first game, which meant lots of pressure and a psychological disadvantage. italy lost 3-0.
In a way the schedule has totally fucked them - allowed Norway to get a head start AND threw Italy in with their hardest game on the group in the first game.