There were times and places in medieval europe, where simply possession of certain items such as swords or metal armour, was a no-questions-asked death sentence for a peasant. The history buffs might want to weigh in on this, but I'm pretty sure the weaponized guy in the tavern waiting to be hired is the stuff of D&D.
Depends on how strongly controlled an area was. In the core regions of France during the reign of a strong monarch with peace on all the borders? No way in hell. In the borderlands that England and France were fighting over for a few decades, with troops having lost officers and looking for someone to provide gold for their swords, very common. And in lands with very little actual control, like Silesia, say, all the time.
