A long time ago, maybe 6 years now, I had an idea about having a "greese pencil" that you could use to make notes, draw proposed stop lines, outline the route you need to take, circle the next objective, annotate those units that need to rest, schedule them for movement to the rear, demarcate the range arc of bombers and fighters. This last one would be particularly useful the way I play. Nothing ever came of my "greese pencil idea". I think they thought about it, laughed about it, and then forgot about it.
If they laughed about it, it would be only because it must be pretty challenging, with the present TOAW graphics engine, to implement. It is a very, very nice idea, to be able to keep notes of what to do, where to do, etc. That's why I tend to suggest alternatives that are nearer to the present state of the game. A simpler (but not that simple) possibility here would be to create a set of counters which could be placed all around the board, more or like those used in ASL to mark units that already fired, residual fire etc. Some key on the keyboard could bring a menu with counters presenting figures like arrows and text (or figures) like "Limit", "target", "stop", "finished", "goal", "moved", "enemy" (for places you know there is enemy units), or whatever. Being able to choose the colors for the counters could be used for planning for specific formations. I always had a problem remembering which units I still intended to move, so I have to cycle through them multiple times. Also, for intelligence info, it would be nice. Sometimes we have seen enemy units crossing by, we know there are enemies around, but we don't have a way to keep track of it. Sometimes we know the strength of a spotted enemy that isn't spotted anymore, and so on. During a game session, with a small scenario, it is easy to keep track, but if we return to the scenario a couple of days later, it would be nice to have some record.