If you reversed those unbu kanji, that would mean "victorious," but I just don't see the kuchou. Kuchou, right? These old kanji usages are so hard because I'm not a linguistics professor (
), so I can only find these read as hisanaga in any dictionary. I'm curious how you read that as kuchou.
I can't come up with any meaning for the top that I'm confident is correct.
I agree that it is a gift to Nobuo san. Most of the names seem contemporary to his, so many of the signers may have been school friends wishing him well as he went off to join the military.
One message on the left means "Strength of a thousand people." One on the bottom says, "Best wishes (or good luck), Nobuo kun" One on the top left may be from a very close woman from the language (mother, grandmother or girlfriend) but one kanji (and therefore the meaning of what she is asking him to do) is unreadable.