I don't know if you've had a chance to look at our reviews of both of these strollers, but just in case you haven't here are the links:
Chicco Tuscany Review,
Inglesina Zippy Review.
In any case, they are both good strollers-- although as you've mentioned, the Tuscany is the winner in terms of value for performance. The only problem with the Tuscany is that it does NOT recline absolutely flat (about 165 degrees instead of the full 180), although there are a number of parents who've managed to use their Tuscany for a newborn infant when swaddled up with proper head support.
The Zippy provides better overall sun protection, has a fantastically easy one-hand fold, reclines completely flat, can handle children up to 45 lbs (the Tuscany can only do 37 lbs max), provides more storage space and comes with a cupholder (although it's really quite useless), and is just a bit more durable when being taken over bumps and such.
On the Tuscany's behalf, it is five pounds lighter than the Zippy, comes with a rain canopy, and is quite a bit cheaper.
Altogether, you'll get slightly more from the Zippy, but you definitely pay for it. Im terms of post-purchasing regrets, it's unlikely you'll end up with many whichever direction you go with either of these two strollers. Although, if something does go wrong with the Zipppy, well, you'll have shelled out nearly three times as much money for it... so the pain might be a bit sharper. Still, the new Zippy's have lots of happy owners, so I'm doubting that would actually happen.
Let me know if you have any more questions.