YOU SAID:
His chair was broken, and he isn't very happy!
INTO JAPANESE
彼の椅子は壊れていて、とても幸せではありませんでした。
BACK INTO ENGLISH
His chair was broken and he wasn't very happy.
INTO JAPANESE
彼の椅子は壊れていて、あまり満足していませんでした。
BACK INTO ENGLISH
His chair was broken and he wasn't very happy with it.
INTO JAPANESE
彼の椅子は壊れていて、彼はそれにあまり満足していませんでした。
BACK INTO ENGLISH
His chair was broken and he wasn't very happy with it.
That didn't even make that much sense in English.