YOU SAID:
This site used to be funnier, when the translations weren't as good
INTO JAPANESE
翻訳があまり良くなかったとき、このサイトは以前はもっと面白かったです
BACK INTO ENGLISH
This site used to be more interesting when the translation wasn't very good
INTO JAPANESE
このサイトは、翻訳があまり良くなかったときにもっと面白かったです。
BACK INTO ENGLISH
This site was more interesting when the translation wasn't very good.
INTO JAPANESE
翻訳があまり良くなかったとき、このサイトはもっと面白かったです。
BACK INTO ENGLISH
This site was more interesting when the translation wasn't very good.
That didn't even make that much sense in English.