Yup, think you've got it exactly. The FIRST job, you're supposed to go back and talk to Mahir before you're allowed out, the others you're just allowed out automatically. I think a user reported "not being able to leave the plaza after job" as a bug, and I "fixed" it, forgetting this difference between the first job and the second and third. And yes, if you don't interact with Mahir there as expected, all kinds of things get thrown off, including the trigger for hypno in combat.
I have reset it to what it was, and it seems to be performing correctly now. I'm going to test a bit more tomorrow to make sure the second and third job are still working as intended, then I'll get the fixed version up. This whole thing has been a head-banging-against-the-wall moment, but hopefully this will be the last "fix" on this issue.