Word. But that's ok, it just creates more opportunities for us 
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depends on your goal
following the chords on the chart will tell you what to play
learning diatonic harmony will give you insight into why the chords work for that key
That is SOOOOOOOO the truth! I've had people ask me what scales or modes I like to use to decide what to play, and my answer is always the same..."The chromatic scale."Learn scales but don't stick to them rigidly because you will drive yourself crazy trying to make things fit which will never be directly explained by scale or key.
I still wonder about the next odd progression Cmi6 - Bb7 - Ab7 - G7, particularly how/why that Ab7 works rather than the AbMaj7
the next odd progression Cmi6 - Bb7 - Ab7 - G7, particularly how/why that Ab7 works rather than the AbMaj7 that I can't explain with the melodic minor, natural minor or major scale.
since you threw down the gauntlet
in a straight C minor key it should be an AbMaj7, that is true.
One theory excuse for using Ab7 would be calling it a "borrowed chord" from some other key (another might be calling it a b5 substitution for a D7.)
If you pick apart the individual chord tones you may also find voice leading implications
but it still sounds like a i - bVII - bVI- V because the triads still work (C min - Bb - Ab - G)
It's the sonic nature of a dominant 7 chord that it wants to go somewhere.
It's usually down a 5th / up a 4th -but it doesn't have to be.
You can generally take any diatonic chord on the way to the tonic, and tweak it into a Dominant 7th, to good effect.
The Beatles did it all the time, and its the foundation of the blues.
Are you talking about passing notes or the higher process of walking from one chord to the next?
Two different things.
Sure, if you are on beat 2 or 3 of the walk - yeah, your logic holds.
That was my point. I was just trying to provide a simple example for the original poster of where knowledge of the key could inform the choice of what to play. I wasn't talking about leading tones at all.