Machining cost

I'm just in overload right now, there are so many options! I wish my dart had a 340 or 360 with it. Why can't i just punch a 318 to a 340 or 360?

Because the blocks are different and the stroke is a big determining factor in displacement. Boring an engine to get more cubes is not desirable as it thins the walls which reduces power under high loads. You bore an engine to get good round cylinders. On a limited budget, especially if you still need headers, intake, carb, I would try and keep the existing crank.