Good post, Holygr4le...
This is undoubtedly tied in with some of your items below (safety, arenas), ticket pricing for the local market, etc.
Though not entirely Serie A, however. I can recall how much Japanese and Korean establishments prepared for English soccer fans during WC 2002 as if General Montgomery's tanks were heading into town.

Yeah, this one is a classic. Vinman and I stopped counting how often we heard people cough into open mics. Not to mention the dead air for long periods, and only occasionally do they seem to offer something so sophisticated on their broadcasts like a game clock and scoreboard.
Part of this, IMO, probably has to do with city-owned stadiums. Compare with the EPL where there is the concept of team ownership of the facilities. And when you build stadiums with city ownership, inevitably they get built to hold down maintenance costs. So ultimately they look ugly and bare. But the upside? You save a few bucks because all you have to do is hire some minimum wage guy to hose the place down as a means of sprucing up the place.
It's no wonder the Champions League final would never venture down into the peninsula in this state.
Barring club ownership of facilities, however, perhaps some hopes can be pinned on Italy's Euro 2012 bid. If it could do what Euro 2004 did for Portugal, there's definitely something to be salvaged.