Hello!
I'm from Italy. It's not about the country (of course shipping to Italy is safe!), it's about people...i mean,scammers are everywhere in the world!
Your italian buyer CAN'T HAVE A PAYPAL CONFIRMED ADDRESS BECAUSE NOONE IN ITALY HAS IT,Paypal doesn't provide confirmation here and in most of Europe countries.So,check it very well!
About the custom restrictions,yes,there are many,some of them truly ridicoulous (knitted items,toys ecc) BUT i always purchased leather items and they never got stuck in customs,despite the restrictions.So,no problem about this,except if you're sending exotic leather items...this "might" be an issue.
Make sure your buyer there will be custom fees,quite high here! (i just paid around 65$ for a 159,90$ pair of shoes).
Be sure to ship with signature on delivery and,possibly,insurance....but these things are the same for every other country,not only Italy