So, I missed him early in the game, but eventually I came back to the building across from the courthouse and talked to Azrael. So this started up his quest "Watcher in the Wings", which I'm assuming means you need to find him various times across the city or whatevs...

So my question to people who have started this question is how this works. Will he trigger at certain parts of the game and appear on the map, or is it just a matter of finding him? Are there any tips you can give for spotting him? Because he shows up just like an unarmed enemy on Detective Vision, so it's tough to distinguish him from another baddie.

He shows up on the roofs in 4 spots, 1 spot in each outside zone (Indy District, Amusement Mile, Bowery, Park Row) Once you find him he won't spawn in a new spot until a certain amount of time has passed, so you're better off working on a diff side mission or continuing main story for a bit. If you want exact locations let me know.

just completed that mission. other than the first occurence, i've always found him on pure accident and while i was in detective mode cuz i would see this one "blue" guy just standing on something and im like "why is that guy just standing there" (cuz they usually patrol) and then i'd turn detective mode off and then he'd just be standing there all creepy like...:(

@Cr0ssbow:

Thanks, man. If I get stumped I'll resort to begging for exact locations, but I just wanted to make sure that there was some kind of context involved on when he shows up, so I don't go crazy just searching everywhere for him. I'll let that quest happen in a more organic way.

@hbkdx12:

He definitely was a bit unsettling when I first ran into him, especially since he didn't really trigger a cutscene so much as just started talking and then disappeared. But Azrael's a cool character, so I'm more excited that he's even in the game.