I've shipped lots of things to Italy with no issues due to the old prohibitions
in fact I just returned from my annual visit to Italy and they always sell MLP , dolls, fabrics ..really all sorts imported from all over the world and all kinds of things in the shops all over Italy that they wouldnt have been able to sell if that rule was still in place. I dont think that you would have a problem shipping the item to him if you wanted to go ahead with it, but send it with tracking if at all possible so there is less chance of it going MIA
Plus some Italians are not that patient when it comes to waiting for items to arrive so tracking helps with that as well
I can do a bit of Italian and i know a decent internet translation site if you still need help and you cant get hold of an actual Italian member to help you