Here are the next concepts for several of the answers I have been working on. They are in development, I still think that they could be pushed even more in terms of a child's imagination. But here is what I have come up with so far for each answer ....
"Every time I save a goal I get more money"
" A Dollar "
"I am gonna play for west ham"
The concepts below are development of my previous post, but with changes by sticking to the rules of child's imagination and West ham.
" I gonna be the captain"
This concept I have changed the telescope to a just a cardboard tube and added the West ham badge to the bandanna. And the concept below and the idea I have settled on is having Tyler dressed up as a pirate with a cardboard sword, playing around and then knocks over the C.