Try any guitarist who uses emotion over speed & technique. Page, Townsend, Lee, Hendrix, Beck etc fro the 60's 70's.
The arrangement issues - why not make a wave of the song & edit out the silly noodlie bits & play it back to him explaining that the sections need to be joined rather than seperated by a bridge.
You could also try slicing up the piece into the various stylistic elements then joining those elements together to demonstrate how they fit each other but not the entire piece as in "These three sep stylistic elements have the makings of three great songs."
Pick any good BAND recording that has a bridge played by the ensemble which demonstrates the role of the bridge (stylistic or key change gradulayy introduced)
Alternately mute the silly bits & have him wail at it with a bluesy improv based on the melody on a new track play it back at him &&&&& the band. there area couple of thise bits so diff instruments could take an opp to extemporize.
Lee, I didn't mention it before but WOW you capture sound well!