Hello, knotty! 
I’d recommend teachings from Ajahn Brahm and Ajahn Brahmāli on the Ānāpānassati Sutta. They hold generally the same interpretation (the latter being a disciple of the former), but they are also independent thinkers and practitioners. Also, the book linked above by Bhante Sujato for a more general overview that can be tied into ānāpānassati specifically.
Ajahn Brahmāli would give you a more technical, text-based analysis. Ajahn Brahm would give you a different flavor more matter-of-factly and experiential with similes and the like. Some of the things you’d find in those interpretations would be like:
As to the third tetrad, that is about developing samādhi and jhāna (as cittānupassanā primarily is). The final phase there (which says they train to ‘vimocayaṁ cittaṁ’—‘liberating the mind’) is a reference to ‘cetovimutti’ (liberation of mind), a term referring to jhāna states. That follows the step explicitly mentioning samādhi.
The suttas say that someone who experiences samādhi will naturally know and see the truth without needing to make an intention or act of will (c.f. AN 11.2). Just that is cause for reflection. Then, the last factor of the eightfold path is sammāsamādhi, defined as the four jhānas. The suttas explain that right samādhi will produce the resultant right knowledge and liberation, which are not included as path factors but as natural results of the path.
So one thing to keep in mind would be that something can be known by its effects. If someone says they have a pear tree that is oddly growing apples, I’d question if they really had a pear tree there.
Another example would be to imagine that someone in Plato’s allegory of the cave, who has never been above ground or seen daylight. If they went above ground for the first time, they wouldn’t need to make an act of will “may I be amazed and discover new things!” The sheer power of their new experience would contain all the data they need to just naturally inquire into the new amazing things.
Likewise, if someone says they have reached jhāna (culmination of the third tetrad) but are not finding insight, it would be quite questionable if they really had finished the third quarter, assuming they had learned about impermanence, four noble truths, etc. and were interested in those topics. The other possibility would be someone with wrong view who views those states as Brahman, God, and so on, but that’s very unlikely for a well educated Buddhist practitioner to blindly assume. If it isn’t coming naturally, the previous tetrads almost certainly need more development. That’s also where different views of jhāna can be put to the test in a sense. If it’s the real thing but doesn’t lead onward as the Buddha said it would, it’s very likely something before what the Buddha meant.
Otherwise, the Buddha’s simple instruction should be more than enough. ‘Contemplate impermanence.’ If it doesn’t automatically occur to the mind what to contemplate, just that should become very clear if the mind has been made ready. Like someone coming up from the cave being told “just look around you” to experience the daylight and objects there. Or someone who doesn’t know what a pear is just being told not to look at the trunk but look by the branches for fruit.
All that said, I apologize if it wasn’t really what you were asking for!
Wishing you all the best!
