Just fill the pot 7/8th of the way with stuff and then top with water. That's how much you'll get.
When you freeze it the aromatics tend to go away, at least that's my experience. So when you use it you might...
Of course, but there are ways to make it easier. How do you intend to do it? I would make the pot pie filling first, then make the bolognese sauce, then make the pie crust, fill the crusts and bake, start the rice, boil the...
It's much easier to screw things up than do things correct. Tomatoes are meant to be juicy, and if the type you have is not meant to go on a sandwich then leave it off the sandwich!