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Cada vez que enfrenté peligros lo hice con la cabeza en alto.
Y cada vez que hube terminado un examen, dormà una siesta en mi pupitre.
Common speech tend to use past simple/past simple and imperfect/imperfect, but that's not written in stone.
About
mirar afuera (where your sight is "pointing")
mirar fuera (the "place" you are looking)
Both are interchangeable almost always, and there are regional preferences. About your example, I prefer "cada vez que miraba fuera estaba lloviendo" because what is "fuera" is not a particular place but the opposite of indoors; but that is just an option.
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