Just to be safe make him captain.
Is his quest multiple days? Also, does his quest appear on consecutive days?
I used him (Kan Ra), fought Kim Wu on my first day and am on day 8 and nothing new for him has popped up.
It is a one and done quest. You need Kan Ra to fight Maya. You fight her, and I think answer a question, then you get the daggers.
This might sound messed up, but the way i plan on doing it is passing days until I get her or day 10. If i get to day, then I plan to restart and repeat.
I got daggers tonight
Hisako (captain),
Sabrewulf and Kan ra were on team