Sorry I got here late!
@ Badger Finn: The guys you have already been talking too are a lot more savvy than I am about this sort of thing. They will probably be the most help.
@ Reece and von Manteuffel: I have all the dates set to the same - 19390101. I use the Random folder only for files I want to change at the game's startup. A while ago, with JScones's help, I did the 'Randomized Loading Screens' mod. It had 100 folders and put up a different loading screen every time you start the game. It also randomized the dockside band music (9 different songs) and the Navigation Map background (three different screens).
For everything else, especially date-based gramaphone songs, I use the Date folder, and I'm pretty sure it does drop the old stuff when new stuff is installed. At least the 'Radio' file changes, since it has the same name it has to.
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