The picture is rotated 90 degrees to the right. The Japanese words are written horizontally there.
The line of the white characters upper "JAPANESE" means "the Government of the Greater Japanese Empire".
The one under "360" at the top of the picture is "There is ~" or like that.
The last character of the line under "10" at the left end could be "month/Moon" or "day/Sun".
Anyway, it seems to be written by someone who actually didn't know Japanese, except the stamp-like "the Government of the Greater Japanese Empire", of course.
Those are just fragments of sentences. If that's a single sentence in the order 2 -> 4 -> 3 -> 1, it would mean;
[the name of a person] is very good at Japanese. He/She cracks a joke when it's least expected, and makes people around him/her laugh.
It has nothing to do with a map, either...
Actually these 4 screen shots area all inside this map at different location. I'm done of this crap map. This keep hunting for many years for what exact means all Japanese symbol inside it. Anyway Thank you very much Sir for your explanation, Appreciated a lot.