I appreciate the discussion. It’s encouraging to hear that these things shouldn’t be overwhelmingly obvious to a beginner. Thanks to TazWake’s response before and now with the addition of other responses, I feel much better about not seeing the route right away.
My approach so far has been to just get as far as I can, collect as much interesting info as I can, and then peek at the writeup, even just to see the Skills Required/Skills Learned and I read up. I slowly work through, take notes, etc. until eventually I can get the flags. As another challenge to myself I like to not submit any flags unless I can reach them without a walkthrough. Not so much to memorize the steps but to solidify the things that stand out in a system so that I can recognize and give me a lead in future machines.
Having a lot of fun with it so thanks again for the encouragement!