Failed Career: Beggar

You Get

A sling, crutches, dirty rags, a beggar’s bowl.

Family Business: You were born into it. Your parents raised as beggars, and you followed in their footsteps. At least one of your parents are still out there, with their can and their beggar’s bowl.
Cheated: Everything rode on that bet and you were sure to win, but somehow the house was stacked against you. You swear you’ll get back at your rival some day.
Asceticism: you follow a faith or philosophy that disallows you from owning more than a few things, needing to rely on the kindness of others. The organization you follow is possible to be called on from time to time.
Profit: Its actually very lucrative, take the max amount of of money for a starting character.
Doomed: ill omens followed your every step. You’ve never been able to hold steady work, but you’ve picked up on secrets others wish not to know.
Beggar’s Guild: You hold membership in a secret organization of spies and information brokers. You can tap into a network of unnoticed people who readily trade in knowledge.

A Good Friend: A faithful dog that always seems to have a scent for extra scraps or an opportunity.
Everdripping Cap: One a day when you turn your hat upside down, it will produce one pint of low-quality ale. Unfortunately your hat isn’t super resilient, so its always soggy and reeks of alcohol.
Dire Catfish Catcher: An impressively long fishing pole you swear can never snap, with an impressive tale about a fish just as big and resiliant.
Emergency Tooth: A wooden tooth you can pop open. Useful for storing a few drops of a potion. Contains one store of a fairly potent healing brew – restore 1d4 HP when you’re able to pop it open.
Leomund’s Placid Pile: A pile of rags that you’re able to crawl underneath, whereupon you find yourself in a pocket dimension – a small, modestly stocked hut is contained within. Unfortunately anyone who disturbs the pile ejects you from your cozy home.
Spirit-Scaring Spit: One small box of chewing tobacco that otherworldly beings find extremely distasteful. For some minor spirits spewing the chew directly onto their face is a semi-reliable form of banishment. Only one use remains.