I don't know... He's in Florida, a long way from Philly. I'm originally from the Philly area, and "A Philly cheesesteak with onions on it and mayonnaise and fries and 20 oz. of peppers" sounds entirely reasonable. It'd be worth just about anything.
OTOH, asking for a Pepsi, that's insane. Gotta be Coke. Or a beer.
For me, it would be a roast pork sammich au jus with broccoli rabe in garlic and oil on a Sarcone's hoagie roll. Like they made at Tony Luke's before he went to jail for tax fraud. And yeah, Coca-Cola.