If "olive" only refers to eggs that are very dark green, I think your "Olive Eggers" may just be laying green eggs (especially the lighter one.)
Yes, breeding the hens that way does sound like a good plan: one pairing for the lighter blue/green shades, one for the darker.
That would obviously...
Oh, good. Some people seem to think a hen's egg color actually will change if they put a different rooster in the pen with her, which is why I thought you were asking that too.
If she lays olive eggs, it is more likely that her daughters will lay green not blue, but it is not a certainty.
If...
I don't have answers for all of your questions, but I can help with some of them.
Daughters would probably lay green eggs of various shades. There is a chance of some daughters laying actual blue eggs, or ones dark enough to be considered olive.
Feather colors: you might get 50% chicks that...