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I believe you may be overthinking the process a little. Tony will sometimes mention a song or songs in his introduction to the challenge and he may invite the audience to think of some songs where they have noticed the same feature he is describing. This doesn’t imply some magical association of each song in the challenge rotation.
What he teaches us day in and day out is to hone your skill the 5 aspects of guitar playing: Technique, Licks, Improv, Rhythm and Chord Progression. Once you have grown sufficiently in these areas it will be much easier for you to learn any song that you want to learn because you have learned the core abilities required.
The teaching isn’t so much song specific, although frequently the lessons are based on certain songs, the goal is for you to grasp how to apply what is being taught to other songs.