-UPDATE-

For anyone who has a similar situation in the future and is crawling through old forum posts trying to figure out if they can make it, as I did, I wanted to make an update of what happened.

He decided to get the Australian working visa, and it was issued to him the next day, which was fantastic. He gathered as many types of proof of intent to return to Italy as he could (bills mostly) and I emailed him an itinerary of our plans for the time he would be staying here.

With all this information, he talked the US consulate in Florence, who told him that to their knowledge, it wouldn't be a problem for him to try again.
I also called Border Patrol and Protection and talked to an agent, explaining the situation (without mentioning our names of course) and they seemed to think that he would be okay to cross.

After an incredibly anxious week, with lots of doubts and fears, he finally flew.
His POE was Newark, NJ, which was scary in some ways because if here were to be denied, he would have to fly back across the ocean again....

When he arrived, he waited in line with everyone else, and was of course taken for questioning when it was his turn.
He talked to many officers, each asking pretty similar questions to ones he already answered. But they asked him pretty much everything you could think. They asked about his family, my family, his life, my life, just really grilled him. And he answered everything truthfully and poignantly. He said that they were all very calm and nice about the process, but it was still intimidating. He eventually just told them the whole story, from the first occurrence until now, and in the end, they let him pass. It was such a relief to see him walking out from the arrival area. They even got him his luggage so it wouldn't be circling around and around by itself. They questioned him for about 30 minutes or so, but with the truth and his preparations, everything turned out just fine.