I can't see that it's worth worrying about. There is little, if any, difference between thinking of it as (Many of) (my questions), (Many of my questions) and (Many of my) questions- the meaning is identical. My modifies questions and many of modifies that- you could look at them as separate entities or chunks- many of is dependent on my in the sense that many of questions doesn't work. What I don't get is the insight that this will lead to.