9th grade chinuch curriculum

I'm reading a blog post and I think this quote highlights something that I'm having trouble with in Chana's chinuch curriculum.

The Jewish educator violates [important chinuch principles] by educational methods which...Try to do the impossible — namely, to give the students genuine possession of the truth without ever really perplexing them first by the problems or issues which the truth resolves — and this requires a vital experience of error, for genuine perplexity is usually killed along with the dummy opponents who have been made into straw men for quick demolition. 

Chinuch goals:

Love of Torah
Love of learning
Commitment to Halacha
Ability to read and understand text
Desire to read and understand text
Mastery of mefarshim
Ability to think deeply about pesukim
Halacha
Torah Shebaal Peh
Nach
Tefila

Right now our chinuch consists of sitting down together every day.  I choose a topic and we do it until she wants to stop.  Some days I choose more hashkafa oriented topics (like ben sorer umoreh) and some days I choose more bekius oriented topics (right now we are going through some of my source booklets from high school on ben adam l'chavero mitzvos), and some days I choose more text oriented topics like a Ramban.  It's haphazard more than organized because Chana's interest varies and I have a bunch of different goals I want to match what we do to her intellectual and emotional moods and also to focus on different skills and areas.

I think her Chumash class experience in high school turned her off to Chumash. We did the Mara story with mefarshim last month (I think we got a nice mix of skills and analysis and enjoyment of major questions and understanding of the story in the overall perspective of Chumash) and she didn't mind that.  But when I wanted to do other parts of Shmos (since that is the book she was learning) she resisted strongly.

I am finding that preparing for learning with her serves me better than being unprepared.  It's better if I have a list of mefarshim that I want to do and if I already know what all the words mean.  She loses interest and patience if I look things up while she is sitting there.  (Which reminds me to look up translations of Pesachim 113 and 118 on lashon hara because there are a couple of Aramaic phrases I don't understand.)

But back to that paragraph I started with, I think that it has been difficult for me to perplex her with problems or issues that the truth of Torah resolves.  She thinks a lot and has often already thought about perplexities and has a theory about them.  So she is not really feeling the question.  And she is not finding that the Torah is truth that resolves existential conflicts.  Something to think about.