I'm unaware of any tool to do what you describe.
I have real world maps I use to remind me of historical routes and times.
I also place Xs using the pencil at the location of important events in the game as I play. Like you say, not every mission or career plays exactly the same.
I see no value in keeping game information between patrols that my historical maps do not provide because the information will go away anyway.
If, however I cared that much to track that kind of information, I could always screenshot the Nav map once in a while.
-Pv-
|