Just wanted to make sure, but if these are played at the same time, it would be a roll off, right?

No. Sorry About the Mess is actually a zero pip. Cunning only reduces the effective pips of a command card if there would be a tie, and zero pips naturally beats 1 pip. This is why playing, say, Annihilation Looms doesn't result in a roll off with other 2 pip cards.

The best way to think of Cunning is that it reduces the pips by 0.5. Because for example reducing a 1 to 0.5 beats other 1 pip cards, but it doesn't beat a 0 pip.

Thanks!

If Han's pimp has the same "shoot first" policy as Han has, I think Han's pimp will win, if the two pimps ever met.

Cunning only comes into play on a draw, which the character with cunning wins, Han doesn't have a 1 pop as noted. Currently if you have cunning the only roll off you can have is if both of you have Krennik or Count Dooku.