This is Russian military officialese.
Your excerpt is apparently a part of a document (план-конспект) describing a training session and defining its goals, steps and methods.
In this context, учебный вопрос just means "topic": something the trainees are going to learn during this session.
Уяснение задачи is something like "objective clarification" (for the lack of a better term; I'm not familiar with English military jargon).
This is a skill of reading and processing orders received down the chain of command, understanding what exactly does and what does not the commander want from you and your regiment.
Оценка обстановки is "situation assessment": where you are, what do you have, and how can you use this to complete your objective.
These two skills are what the trainees are going to learn and what the whole session is all about.