Project 5 Masking

We had to make a video utilizing masks in After Effects. I decided to tell a a little narrative of someone (the audience) looking through a telescope at a boat on the water. Then the telescope disappears and suddenly a map pops up. It becomes animated and points in around about way to get to the X. I wanted the environment to be very texture oriented with a watercolor texture applied to all the waves and the sky. The outlines for everything were done with a crayon brush tool to look as if its a children's drawing. I was wanting to get across the idea that the audience who is assumed to be older is forced to look at the way a child sees storytelling and adventure archetypes. I had many problems with the map animation because of the masks. It wasn't difficult to have a stroke dotted line mask appear to show the "steps" on the map. What was difficult was when I wanted to have the boat follow the motion path of the dotted line. I had to finally end up drawing the path in illustrator and importing it onto the boat's position to get it to work and then manually go about editing the path so that it lined up with the dotted line. For some reason it just would not let me copy and paste the mask path of the dotted line onto the position of the boat. I need to look into it and figure out what exactly prevented that so I won't have to waste time going through backdoors to get the same effect.