Just remember that caulking the siding shut doesn't give moisture freedom to move in and out, creating a potential mold issue and a problem with paint adhesion...
My rule of thumb on estimating is to add 20% per floor. If the house is a 2-story, the footage above gets additional consideration, a third story gets 20% above the second, etc...Makes ladder hopping all that much more enjoyable...
...Can't really give you a price. I'd have to see it.
Good luck