"So my question is, does WIND even offer pre-paid plans for someone in my situation? And if not, are there any other pre-paid cards that have decent data plans in Italy?"
Yes, and Yes
WIND and TIM have a variety of data offers.
Over the Summer I used WIND 5gb for 30 euros per month, and TIM 9Gb (not for use between 9am and 5pm Mon-Fri), for 25 euros. I used them in an HTC TyTN and a datacard in my laptop.
I think you would have to buy the SIMs when you get there, and they dont sell them in Naples or Catania airports.
Try and identify a shop to buy the sim from before you get there - I didnt find it easy. Where are you going first?
Cheers
Richard