Source: Curse of Strahd: Optional Backgrounds

The Iron Route, once the primary trade route between Phlan and Zhentil Keep, used to be a site of extensive banditry until the Phlan’s recent occupation. Your time as an erstwhile bandit has given you plenty of experience in the saddle and a knack for acquiring and appraising other people’s mounts, pets, and vehicles among other things. This particular set of skills has become very lucrative for you by working for the underground as a horse thief for a local guild of thieves and other shadowy organizations.

Skill Proficiencies: Stealth, Animal Handling
Tool Proficiencies: One type of gaming set, vehicles (land)
Equipment: A set of dark common clothesValue:5sp Weight:3lbs, pack saddleValue:5gp Weight:15lbs, burglar’s packContents:
1 Backpack - Value:2gp Weight:5lbs
1 Bag of 1,000 Ball Bearings - Value:1gp Weight:2lbs
1 10ft of String
1 Bell - Value:1gp Weight:0
5 Candles - Value:1cp Weight:0 (individually)
1 Crowbar - Value:2gp Weight:5lbs
1 Hammer - Value:1gp Weight:3lbs
10 Pitons - Value:5cp Weight:0.25lbs (individually)
1 Hooded Lantern - Value:5gp Weight:2lbs
2 Flasks of Oil - Value:1sp Weight:1lb (individually)
5 Days' Rations - Value:5sp Weight:2lbs (individually)
1 Tinderbox - Value:5sp Weight:1lb
1 Waterskin - Value:2sp Weight:5lbs
1 50ft Hempen Rope - Value:1gp Weight:10lbs
and a pouchValue:5sp Weight:1lb containing 5gp.

Feature: Black-Market Breeder

You know how to find people who are always looking for stolen animals & vehicles, whether to provide for animal pit fights, or to supply some desperate rogues the means to get away faster on mounts during an illegal job. This contact not only provides you with information of what such animals & vehicles are in high demand in the area, but also offers to give you favors and information (DM choice) if you bring such animals & vehicles to them.

Iron Route Bandit Personality Traits

d8 Personality Trait
1 If people leave their gear unsecured, they must not want it very much.
2 I feel more comfortable sleeping under the open sky.
3 I always pre-plan my escape should things go bad; I always like to have an exit strategy.
4 I tend to give animal owners breeding and care advice whether or not they want it.
5 I lost a pet as a child and sadly reflect on it to this day.
6 I always form a powerful, emotional bond with my mount.
7 I recoil at the thought of killing someone else’s pet or mount.
8 I prefer to hang to the back of a scuffle or discussion. Better to have my enemies in front of me.

Iron Route Bandit Ideals

d6 Ideal
1 Loyalty. Never bite the hand that feeds. (Good)
2 Unpredictability. Keep your enemy guessing and off-balance like a confused deer. (Chaotic)
3 Power. I strive to become leader of the pack at all costs. (Lawful)
4 Freedom. I bow to no one I don’t respect. (Chaotic)
5 Resourcefulness. Our wits are our most valuable resource in troubled times. (Any)
6 Unity. Lone wolves fail where the pack succeeds. (Any)

Iron Route Bandit Bonds

d6 Bond
1 I cannot leave a harmed animal behind; I must save it or put it out of its misery.
2 I leave behind my own personal calling cards when I do a job.
3 I do not trust people who do not have a pet, mount, or furry companion.
4 The pelt I wear on my back was from an animal that died saving my life. I will always cherish it.
5 If my pet does not like you, I do not like you!
6 Once you’ve ridden with me and fought by my side, I’ll be there for you odds be damned.

Iron Route Bandit Flaws

d6 Flaw
1 I talk to animals; I believe they understand me, even if they do not.
2 I growl at and bite anyone who gets too close to my food while I am eating.
3 I strongly dislike enclosed spaces and require intoxication or firm encouragement to enter them.
4 I robbed the wrong caravan once. The owner is a powerful merchant who holds a grudge.
5 I’m an inveterate gambler.
6 I judge people based on how well they stand their ground in a fight. I got no time for cowards…