I read your questions a few times but each time something new pops up to me, so one time I’m thinking you would like to know more about the source of their knowledge, one time I’m thinking you are inquiring about the possibilities of such commands, and another seems to pose the question of what skills the servitors have access to?
Your approach seems pretty good to me, it seems like with some more communication you will start to get the idea of it.
Few things I wanna mention though,
An understanding of the concepts, being the umbrella to what the commands are might be more needed to bypass some of these concerns.
For example, if we are talking about chess, consider having the servitors learn more about the element, nature, and role of time.
Being that, in the moment, you want to receive the answers instantly.
On books and information, these are accessible to servitors through different ways than just the alphabet or the physical book. Experiment with communicating the concept and the topic of the book, the author perhaps, and let them ‘extract’ these information from wherever they find it possible.
You can even give them a task to look for the ‘sources of information’ present in all realms and act based on the relevance, accessibility, etc…
Other than that, every question you have is Yes 
Example:
Do they have access to subconscious? Yes
Do I send them to learn chess? Yes
Do I teach them how to use other person’s cues? Yes
Do I tackle outcomes and progress? Yes.
Do I assign certain skills for them? Yes
Yes
You get the idea
Pass by this thread also:
How to Better Connect with Servitors/Audios/Items/Mandalas
And this gem written by @Saan