Well, I think the 1/2 cup of olive oil might have to be counted. There are 7 servings in this recipe, so divide 1/2 a cup by 7. If it's more than your allowed 2 t. of healthy oil, then you'd have to count points for it. Either that or halve the dressing amounts, and just eat it with less dressing.
The olives I wouldn't worry too much about. There are only 10 in the recipe, and again, at 7 servings per recipe, that's only a little over one olive per serving. I'm not an olive-lover, so I'm not sure how big kalamata olives are, or exactly what they are. Black olives are Core, right?
Turkey ham is very lean, and is not a deli meat. I find mine right next to the regular ham. Jennie-O makes a great turkey ham. It comes in big ham-shaped chunks, and looks and tastes pretty much like regular ham, except it's a lot leaner.
Let me know how it turns out if you try it,