Upon further discussion of the matter with my brother, I think I was wrong.
Robin Hood is the wrong way to play Midnight+ACKS. It's the stupid-hero way, and it is a good way to get killed in short order.
The right way is closer to what my Midnight True20 players did back in 2011 or so. That party of escaped slaves had a Dornish former mercenary, a gnomish channeler, and a halfling thief. They put the halfling in chains, attached the gnome as a mercantile aide, and walked right in to the Governor of Highport's keep looking for work. And work they got, in the name of the Shadow - temporary service with a legate who needed a champion for a challenge by combat for the mercenary and miscellaneous servant's work for the others, which allowed them to pass unnoticed and intercept the delivery of their own wanted posters. Then they sprung a crew of gnomes out of slavery, sabotaged the harbor defenses, walked on to a ship and said "Hello, we're here on orders from X legate with our crew of gnomish slaves," and sailed on out like nothing was up, with the city of 20,000 orcs none the wiser.
That's how you play Midnight. Deception, cunning, and occasionally giant cojones / refuge in audacity. Midnight is not a place for heroes after the paladin in shining moral armor model, but rather for rat bastards who lie, cheat, and steal to get by.
Very suitable for old-school play, indeed. This is combat as war brought out of the dungeon and into town. I might need some new statistics for enemy leadership (loyalty, integrity, cruelty, stats like that) as guidelines for making their behavior consistent... and I will need to look at and build towns as another adventure locale. Though given some experiences with ACKS, Tim and Drew might argue that's something I already do.
I also realized that ACKS' solid values for mercantile goods would be extremely useful in a Midnight-like barter economy, since you could use them to award consistent XP for hijacking caravans and ships, as well as as currency. The other wonderful thing is that with Domains at War, I can figure out exactly what sort of orc-density a territory would need to be considered 'controlled' by the Shadow, what level of legate might command a company of 120 orcs out hunting for rebels in the woods, and how to reasonably resolve strategic wilderness movement, detection, and combat between those 120 orcs and a band of Merry Men, should the PCs decide to do the stupid, heroic thing, or to lead double-lives as collaborators and conspirators with both the Shadow and the Resistance. No fiat about it.