VDV won't fit in a straight 4-4-2 as a left winger, but he would fit in well there as a forward. But we have the forward position covered up so no need there, unless we are planning for a 4-3-3.
But VDV ideally would benefit from playing in a 4-3-1-2 as an attacking midfielder behind the 2 forwards. This system would be great not just because it utilizes VDV to the max, but because it is the position where Giovinco would shine in as well. But for that to work you are going to need a very good attacking left back to run down the flank...something that Molinaro is not.