For me, the more feral the better

The Barracks are just north (as the crow flies, walking is a bit more indirect) of the taverns. North of that is the temple and magic academy, and finally in the far northeastern corner is the Castle with the bank in its basement.
I mean, you *are* doing some serious zig zagging. The Thornwall's outshoots have turned Thorncity into a labryinth. But Corvin has the city memorized due to his training, so he'll have no problem hitting the places he needs to hit efficiently. And if he gets lazy, he can always climb and move along some roofs.
No need to apologize
Probably a few days before he got there. Maybe the 10th or so.
This infers that Benjy certainly didn't tell his family he'd been discharged and that he might have even handed in the confirmation himself if he told them he needed to be back for the 8th. Then you have two days for the priestess to get to the village.She gives him a meaningful look. "The shrine I stumbled on did not look that neglected. And Benjy had been visiting only a few weeks before, before having to report back to his unit only a few days before the priestess came."