Perhaps your comment about “Isn’t all awareness choiceless” depends on how we define awareness (i.e., semantics). Perhaps all awareness is choiceless, but for me, the key point I am trying to convey is that Buddhism encourages us to direct our attention (or awareness, depending on how you want to define it). I see that you mentioned something like this earlier when you wrote (earlier in this thread):
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Yes, I agree about satipatthana being directed attention or awareness, I was thinking more about what happens “post-awareness”. Noticing things, but with a sense of detachment, therefore being less likely to react. This can create some internal space, allowing the possibility of a meaningful choice.
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A very interesting sutta on the (non-)direction of attention is AN8.63. Here is the refrain.
AN8.63:3.1: When this immersion is well developed and cultivated in this way, you should develop it while placing the mind and keeping it connected. You should develop it without placing the mind, but just keeping it connected. You should develop it without placing the mind or keeping it connected. You should develop it with rapture. You should develop it without rapture. You should develop it with pleasure. You should develop it with equanimity.
What is remarkable about this sutta is that the refrain repeats again and again . The progressive refinement described by the refrain is itself successively applied within multiple contexts (e.g., the releases of the heart, etc). The progression spirals onwards, circling repeatedly to equanimity within each context. In other words, it’s not linear.
Indeed, it would appear that the sutta suggests that we apply the progression in each context we find ourselves in. The notion of “attainment” evaporates with this perspective since a new context might very well have us start again with “placing the mind and…”
That would also satisfy the never-ending effort:
DN33:1.9.34: To never be content with skillful qualities, and to never stop trying.
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Thanks for mentioning this. It appears that this sutta (AN8.63), in an earlier section before discussing this progressive refinement, does encourage trained “choiceful” or “intentional” awareness when it says:
My mind will be steady and well settled internally. And bad, unskillful qualities that have arisen will not occupy my mind.’1.8
That’s how you should train.2.1
When your mind is steady and well settled internally, and bad, unskillful qualities that have arisen don’t occupy your mind, then you should train like this…
The refrain that you mention (“placing the mind and keeping it connected”) sounds like the four jhanas, ending with equanimity.
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Indeed, and right in the middle of the refrain we have the marvelous “You should develop it without placing the mind or keeping it connected”. So you see? We have to do it all. 
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Meditative insights do not exclusively depend on meditation instructions and techniques. It is a dependent arising.
Ethical discipline, points of doctrine, rituals, are so many factors that constitute the framework in which meditation takes place. Inner qualities, the state of one’s body, motivation, goals, the place where one practices, one’s companionship, etc. also play a role.
To put it simply, I would say: The more stable one’s framework or background, the safest it is to engage in “choiceless awareness.”
In Chán, we focus a great deal on cultivating the quailties it takes to engage in “choiceless awareness.” It is like training before trekking in a place one doesn’t know yet. In the Lieh Tzu, it says:
“Faced with an obstacle, the unenlightened man begins to think about possible benefit and injury, and ponder alternative courses of action. But this thinking does him harm instead of good… a good swimmer learns to handle a boat quickly, because he does not care if it turns over…”
When one engages in “choiceless awareness”, mind itself ends up becoming the object. More attention is drawn to the mirror-like mind than it is to the fleeting images that appear in it.
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