Name: Tokigetsu, Samara
Amount Owed: 250 ryo
Known Information: Tokigetsu Samara is a known drunk, he makes a daily trip to the Kiri Bar atleast once a day around noon to flirt with the bartender, Tsumi.  

Name: Yamata, Renji
Amount Owed: 400 ryo
Known Information: Renji runs a small item shop in the Kirigakure Downtown Mark District, his hours of operation are between 11-8. He shouldn't be hard to find but he's been threatening every representive we've sent. I don't think he'd actually hurt anyone but it's hard to press someone when they have a naginata pointed at you.

Name: Asagai, Ayuuma
Amount Owed: 1400 ryo
Known Information: Ayuuma is a the leader of the Asagai Sharks Mercenary Group. She is rumored to be extremely good with throwing weapons. Her gang often meets in the Pirate Cove. We've sent countless respresentives out there to collect her debt. Needless to say the last one quit shortly afterwards.  This one will be some trouble, but for a ninja, she should be no problem...right?

Samara will try to weasel his way out the debt and he doesn't want to look bad in front of Tsumi. Several approaches will get you the debt, but there's an extra 10 ryo in it if you can make him look good infront of Tsumi.
Renji's debt is up there but his excuse is how hard it is to run his business. Intimidation is a sure fire to get him to cough up the debt. Still he's not necessarily a bad guy, if you can score him more customers he'd throw in an extra 10 ryo for your troubles and who knows maybe you can get a discount later...wait aren't discounts supposed to be less than the advertised price?
Ayuuma is hiding out in the pirates cove with her crew. She's not going to give up the cash without a fight.  Not to worry though, Ayuuma likes to show off her throwing skills. So she'll challenge whoever takes this mission to a marksman game. When she get's close to losing she'll cheat and feign coughing long enough to slyly toss a shuriken at your own. Character with Ace Eye characterstic can spot this cheat attempt, characters with Sharpshooter  will win the contest with ease. 
Once you beat her she's a sore loser and will fork over the ryo, but on your way out she'll throw some shuriken at you, unless blocked it will deal 50 ryo worth of health expenses. Characters with Reflexes can dodge this without needing to block.  Once you return the Asaka Financing Company is so surprised you collected from Ayuuma they throw in an extra 10 ryo for your trouble.