You can’t say that you won a war without putting troops in the conquered area. I don’t think that he could occupy us
for the same reason that the Japanese could not in WW2.
I don't think you or I have any real idea of how this psychopath thinks. Remember, he runs a slave state. He supposedly executes people using mortars, AA guns, and hungry dogs. Would you consider executing people like that? Probably not, because you are not a psychopath.
Kim would probably consider himself victorious if he survived an armed conflict with the US. Every US or South Korean or Japanese death thrown in is just a bonus for him. North Korean deaths are immaterial to him. Think of Hitler in the bunker.
You are probably right.