The latter gives us the opportunity for a few fun threads where Jeri and his goons attempt to get back what's owed him. It might even eventually lead to him putting a bounty on the head of whoever owes him money (assuming they borrowed enough for its return to be worth more than the expense of a headhunter).
Supplying can also be fun. It'll give you plenty of opportunities for new hunt&gather threads. Jeri's a hard negotiator but fair in the end (assuming he's not dealing with bartering newbs, who he will take advantage of).
He may also be in the market for a new part-time lover since he left poor Misha behind in Hesia with barely a second thought. He doesn't demand faithfulness as long as his partner is discreet, but he does demand a high level of personal hygiene.
Alternatively, you could be an old supplier trying to track him down because he owes you money. Of course, if you're an old customer who owes him money, that also leaves plenty of opportunity for him to stumble across you and decide he wants it back right now.