YOU SAID:

I hope a car crushes you in the middle of the night

INTO JAPANESE

真夜中に車に轢かれたらいいのに

BACK INTO ENGLISH

I wish I was run over by a car in the middle of the night

INTO JAPANESE

夜中に車に轢かれたらよかったのに

BACK INTO ENGLISH

I wish I had been run over by a car in the middle of the night

INTO JAPANESE

夜中に車に轢かれればよかった

BACK INTO ENGLISH

I should have been run over by a car in the middle of the night

INTO JAPANESE

夜中に車に轢かれるはずだった

BACK INTO ENGLISH

should have been run over by a car in the middle of the night

INTO JAPANESE

夜中に車に轢かれるべきだった

BACK INTO ENGLISH

should have been run over by a car in the middle of the night