The recent post by
@atwl77 reminded me about this thread so thought I'd update here.
In answer to my question does it eventually click? Yes... But then it's like opening Pandora's box and off you go down another avenue.
I've been working through Autumn leaves, starting with just the chord tones, literally playing up and down each chord, then introducing voice leading. This inevitably becomes predictable.
I've since been introduced to diminished chords, somewhat of a revelation, perhaps it was the months of playing chord tones, but these really perked me up.
Theory is not my strong point, it can take a long while for it to sink in, however my teacher is patient and will explain it repeatedly, importantly what to learn, how to learn it and why, and when to use it.
My teacher is happy with my progress, I'm enjoying learning. I'm told I am 'improvising', to me I'm essentially embellishing & elaborating the melody... I'm now not satisfied as it still sounds like Autumn leaves, so am working on that.
My teacher often uses the analogy of a child playing with a box of coloured building blocks, there's loads of ways to assemble them, improvising is similar.
I've still a long way to go, but instead of feeling like I'm in well above my head I'm now starting to look at, and even get excited about what else I can learn and incorporate.
I might pluck up the courage to do a recording.