All of this is extremely helpful. The problems I was/am having are:
Watching my feet, and I have a hard time telling myself I can "make the gap" in my head. Ollie-ing itself is difficult for me... I have a lot of heel lifting in my boots...
Then definitely try to invest in new boots. Get them fit in a store, don't buy online. Try different brands and styles as all fit a bit differently. Having properly fitting boots will help all of your riding as well as make it a touch easier to progress.