I guess my question is, if both the rocks and sky are darkened equally how much separation is there?
Knowing this is a bit difficult. There are two ways that approximate things, but often, you need to bracket with different filters.
The first is simply to look through the filter and see what happens. The filtering effect is most apparent with stronger filters, but you should be able to get some idea with both orange and green filters.
The second method is to meter through the filter and note the difference in exposure for different areas. The problem here is that meters and film have different spectral responses, so such readings can be misleading unless you do some tests and figure out which way your particular meter/film combination is off. Still it'll give you some kind of idea.
If you're not sure, try a couple of shots with different filters. After a while, you'll gain experience that will help you choose the filter you need for the effect you desire.
Best,
Doremus