Jack 2: Con Artist, +1 CD
Jack 3: Lover Not a Fighter, +1 CD
Jack 4: Fake It 'Til You Make It, +1 CD
Hit Die: d6
Starting Equipment: Weapon of choice small enough to hide under your clothes (daggers and pistols yes, battleaxes no), fancy clothes (3 sets), hireling buddy you convinced to go on this adventure against their better judgment
Skills (d6): 1. Bartending, 2. Etiquette, 3. Languages, 4. Music, 5. Oration, 6. Seduction
I Know a Guy: You have Contact Dice, which are d6s. Spend them to realize you know or get to know someone in a location, and roll 1 die for each feature you want them to have. The extent and usefulness of the feature is based on how well you roll. You can spend multiple dice on one feature to take the highest of those dice. If you roll doubles when making a Contact, also roll a Complication. Spent Contact Dice return on a long rest, or when you enter a new town.
Information: 1. Common local wisdom → 6. Secrets known to few
Item: 1. With some creative thinking, what they have might be useful → 6. They've got exactly what you need and more
Location: 1. Temporary access to a generic kind of place you're looking for → 6. Round-the-clock access to the exact venue you need
Relationship: 1. You met once, a long time ago → 6. You've been close since childhood
Skill: 1. Decent at a relevant skill → 6. Multiple class levels
Status: 1. Trusted by locals → 6. Official title and position of power
1. They want a favor from you before they help you out.
2. They're laying low and can't do anything that'd attract attention.
3. They're harder to reach than usual, perhaps temporarily in prison, or on a trip out of town.
4. They're doing something you find distasteful, perhaps at cross purposes to your aims.
5. They're working with/in a relationship with someone who doesn't like you, who'll be around making their own demands.
6. Their value to you has been misrepresented somehow. Decrease their highest feature by 2.
Once you've made contact with them, you can spend Contact Dice during long rests in their area to either get a chance to upgrade the level of an established feature, or get them as a hireling for (sum) days at the cost of (dice) shares of the loot. If you roll the same level as they currently have, however, roll a new Complication.
Trustworthy Face: If you aren't in open combat with someone, they're going to be a little less hostile to you (but not necessarily the rest of the party) than they would be to your average murderhobo. If you speak their language, upgrade their reaction to you by one category, or downgrade it if you want to.
Con Artist: So long as no one can verify what you’re saying is wrong, you can lie through your teeth and they’ll believe you for at least d6 minutes. You can walk through somewhere unquestioned if you look like you belong and don't act suspicious for at least d6 hours, so long as you don't start talking to people. With a daily rest of practice and study, you can learn the basics of a skill to the point where untrained onlookers will believe you know what you're doing until you fail a roll. Expires on your next daily rest.
Lover Not a Fighter: You can make attacks with Charisma vs. your enemy's Wisdom if they speak your language. If you do, the attack inflicts Stress instead of damage. You may make the penalty for failing the Stress roll changing their reaction by 1, instead of Cracking.
Fake It 'Til You Make It: If you get a long rest of training from someone with levels in a class, you can use that class's level 1 abilities until you fail a roll on them. Can't do it again until you go back and get pointers on how to do it during a long rest in town. You can have access to multiple fake classes at once, but you can't get abilities above level 1.
Reaction Table (2d6)
For when you need to apply Trustworthy Face/Lover Not a Fighter, or figure out the kind of first impressions an NPC gets of the party. Obviously as a GM you can apply whatever bonuses/penalty you want, rule out certain reactions for things like dragons or drow, or just set reactions at your whim.
These can mean different things based on the context! With a shopkeeper, Unfriendly might mean a significant markup for the heavily armed murderhobos who cause nothing but trouble; Hostility might be outright refusal of service. With a pack of dire wolves, Trusting could mean they see a fellow pack, and treat you as they would another band of wolves they're on good terms with.
If multiple individuals in a group have different Reactions, they might fall into infighting or argument between each other. A Jack who uses their Lover Not a Fighter skills to turn a gang of bandits against each other is a force to be reckoned with. Getting a leader to change their reaction is likely to get the rest of the group to change their opinions - or fight each other.