All it takes to go from free citizen to indentured servitude is to over-spend your assets. Your court-appointed attorney will plead guilty for you before you even know you're in debt.
Read the fine print carefully before you thumb-print any contract. Note that the carrier is not liable for errors in shipping.
It's no easier to be an itinerant armsman. A lute and tunic are lighter to carry than an axe and armor.
When the wandering bard and the itinerant armsman team up, life should get easier for both of them.
And it does.