I don't think your plane analogy is a useful way of thinking about writing. If you have to land a plane you can only land it once and it either lands safely or it doesn't. With writing you get unlimited goes and unlimited amounts of edits. You don't get just one attempt. You get as many attempts and as much editing as you need and you can get feedback between edits as well. If you want to stick with a flight analogy, you're in a flight simulator - nothing bad's going to happen if you do anything wrong - and you have an unlimited number of attempts to make the approach, and you can get feedback and suggestions for improvements between each one. And when you've finally done the perfect landing, you can record that one, and that one alone, and all the others get deleted forever (unless you want to keep them).
Your concerns regarding how much readers will or won't get are totally valid and getting your work critiqued and getting feedback will help a great deal with that. Also if you spend a lot of time reading (anything) and critiquing other writers work that will help you hone your own skills in writing and editing your work, with regards to all kinds of things including how much readers will take in and infer about the situation from what you write. Another trick for editing for this specific thing is to take some time away from the project, forget about it for a while, then go back to it and try to read it as though you're a reader, not the author. This isn't a perfect substitute for having someone else look at it and give you feedback, but you will pick up a lot of things and it will help you to develop your ability to tell how much the reader's going to understand from what you write. I would strongly recommend to get your work critiqued by others as well though.
Your concerns regarding how much readers will or won't get are totally valid and getting your work critiqued and getting feedback will help a great deal with that. Also if you spend a lot of time reading (anything) and critiquing other writers work that will help you hone your own skills in writing and editing your work, with regards to all kinds of things including how much readers will take in and infer about the situation from what you write. Another trick for editing for this specific thing is to take some time away from the project, forget about it for a while, then go back to it and try to read it as though you're a reader, not the author. This isn't a perfect substitute for having someone else look at it and give you feedback, but you will pick up a lot of things and it will help you to develop your ability to tell how much the reader's going to understand from what you write. I would strongly recommend to get your work critiqued by others as well though.