It looks to me as a problem with the menu configuration of the game (Bad file...corrupt install...scratched CD??), and the missing file is this: "tooltips.dsm". That file is probably used by the sim in some stations (And crashes when you go there) and always when ending the mission (Which is why it always crashes then).
Anyway try reinstalling DirectX again, in case some of the files are corrupt or have been overwritten by the drivers of something you installed. Reinstalling the game and trying a different screen res could also help locating the problem :hmm:
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One day I will return to sea ...
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