Hi, Peter!!
Right place to ask but you may not like the answers for your buddy.

are you talking about the buddy flying on KLM or AF? nope on all OAL
how are you thinking about getting from AMS to Italy (which city?)

which return city? ATL, DTW, JFK etc

the S4 issue is HUGE in some cases but you have to look at how many options you'll have per airport and how $ is it to stay over if you don't make it.
are you going to sit with buddy? in that case, you have to plan on downgrading your pass to S4
When are thinking of returning? end of August, as well?