Old military expression, dating back to Revolutionary War times. Everybody would try to shoot the guy carrying the flag into battle, as he was a big target. Having a flaggy day means everybody is out to get you, you're having a bad time, or life is just generally rough today.

A cultural and aesthetic mind-state that prioritizes making money, even as an “underground” or “radical” creator. The work isn’t made for money, but it’s the money that matters the most.