The second picture is the correct orientation.
There is only one slogan 祈武運長久 "Hope Your Eternal Good Luck in Battle" on the upper right of the flag. This is the most common one.
The recipient of the flag 八木末？(illegible) Yagi Sue/Matsu? is written on the left side of the slogan.
Only two presenters wrote their position. The lower right one 北迫武雄 Kitasako Takeo worked in Osaka City Waterworks Bureau and the one next to the left of him 出水義雄 Idemizu Yoshio was the subsection chief of the general affairs section of a bureau (illegible).
The rest are all signatures of the presenters.