i would make the kid looking at the guitar. also, the way it is, it's not clear that the dude in the photo is his grandpa - i realize that's the point of the "1943" record, for example, but i can see it being easy for someone to just not know.
hrmmmm, yeah i totally agree with banana that it's difficult to piece together the story. i'm not sure how to tie it all together either...wish i could help more but no ideas come to mind. it's not bad as it is though and i think it might do well in this format.
it's a really cool illustration though, my favorite of yours so far actually image-wise.
I love the fifties look of this illustration. It looks a bit busy to me, but I can see that its hard to get the message across.
You know how multi-platinum awards have several discs as well as an album cover or something? You could combine several of the components of the current picture into one using that idea. Does the kid have to be looking at a toy guitar? Could he be reaching for or staring at the main guitar? Maybe on a stand? (the guitar that is, not the kid)
I think forcing it to link back to Grandpa is pushing the 'viewer' - just a bit of family hero worship (father, grandfather, uncle, whatever) could work.