YOU SAID:
the man entered the room cold rusty flat he sat down
INTO JAPANESE
男は彼が座って部屋の冷たいさびたフラットに入った
BACK INTO ENGLISH
The man went into a cold rusty flat in the room where he sat
INTO JAPANESE
男は彼が座っていた部屋の冷たいさびたフラットに入った
BACK INTO ENGLISH
The man went into a cold rusty flat in the room where he was sitting
INTO JAPANESE
男は彼が座っていた部屋で冷たいさびたアパートに入った
BACK INTO ENGLISH
The man entered a cold rusty apartment in the room where he was sitting
INTO JAPANESE
男は彼が座っていた部屋に冷たいさびたアパートに入った
BACK INTO ENGLISH
The man entered a cold rusty apartment in the room where he was sitting
That didn't even make that much sense in English.