Well, I'd start by having both those types of questions, and some in the middle as well.
Levels:
Hamburg (easy questions)
Abbey Road (middle questions)
Apple Rooftop (hard questions).
or something like that. You could have "seven levels"
I'm thinking even the In My Life question could be in the middle, along with harder stuff about albums and stuff
Then the really hard one could be something like, what does the "seven wonders" lyric in And Your Bird Can Sing refer to? And stuff about the solo careers and pre-Beatles stuff. Like hardcore knowledge.
This sounds really cool, especially if you have enough questions. ...