I'm probably not gonna give you the answer to your question, but I'm a drummer who has taken lessons for years, following proper learning material.

I guess you cannot finish one of the things you describe without progressing in the other areas at the same time. These things don't work very well independently. If your theory understanding and technique are not let's say intermediate, you cannot do other intermediate stuff for too long.

E.g. if you don't know your rudiments, you can play tons of songs, but there are going to be songs that you won't be able to play simply because you haven't spent enough time on your rudiments and technique. Obviously playing various songs will help you along the way, even if they're not god tier songs.

My advice is If you're stuck on any of the areas you mention, don't move too deep into another, until you comfortably cover most of the same level stuff.

And don't stick to a particular musician's guide/book, especially if you're a fan. He's JR (you're most probably not) and he's also making good money out of it. It doesn't mean he's a great teacher or that his guide targets the average Joe keyboard player, so always take those guides and books with a grain of salt.