This is surprising. I used to be like your second student according to my father. He taught me most everything I know, and my brother used to be like your first student.
I found what personally helped me to overcome the insight bridge/gap was I had to read several different books to find the right analogy that helped achieve the "insight".
There are certain things I definitely did not get in the beginning. But after working very hard I got them.
I am curious what percentage can make the jump as I did. Clearly there are certain "epiphanies" to be had. I almost immediately understood "for" loops, but took several years to get pointers and polymorphism each. I know of people who get some or all of these concepts instantly.
There is clearly the appearance of bimodality here, even in just my experience with just how I learned things.
I found what personally helped me to overcome the insight bridge/gap was I had to read several different books to find the right analogy that helped achieve the "insight".