1.

In protected cities, WANTED people shouldn't be able to enter their guilds and be healed by city healers. Doesn't make any sense. I assume those folks are paid by the city, wouldn't they report criminals instead to the guards.

2.

Shopkeepers - a question that can be asked that let's you know if they are out of coppers even during their off hours. Basically so you don't sit until their opening hours only to find out they're broke. Something along those lines.