YOU SAID:

you should have hit him more than once.

INTO JAPANESE

彼を複数回onceったはずです。

BACK INTO ENGLISH

He should have been once more than once.

INTO JAPANESE

彼は二度といるべきだった。

BACK INTO ENGLISH

He should have been again.

INTO JAPANESE

彼は再びいるべきだった。

BACK INTO ENGLISH

He should have been again.