I always like the idea of PCs who don't fit into the regular PC classes . . . especially the various thinky and talky professions (sages and courtiers and whatnot).
What I'm looking at is a variant Rogue, with a scoop of the Expert sidekick class.
So starting with Rogue . . .
Hit Dice Die D8 per Rogue level That'll work.
Saving Throws Proficiencies Dexterity and Intelligence Change to any two? Maybe even more, since the Expert is the guy who manages to survive stuff despite not having the resume?
Skill Proficiencies Choose 4: Make it any four.
Weapons Proficiencies Simple weapons and Martial weapons that have the Finesse or Light property Might just say simple weapons?
Tool Proficiencies Thieves’ Tools Change to any one tool set
Armor Training Light armor That'll work.
Class features:
1st
Expertise - Totally appropriate.
Sneak Attack - Replace with Helpful (Help action as a bonus action)
Thieves’ Cant - Or any other language
Weapon Mastery - Thematically maybe hard to justify, but maaaaaybe. Or just give them the Lucky feat?
2nd
Cunning Action - Totally appropriate
3rd
Rogue Subclass - Well here I am stumped, because developing subclassses is a hassle. Maybe just pick a feat, even if it's from the General list?
Steady Aim - Thematically iffy. Maybe something that lets them Dodge as a bonus action?
4th
Ability Score Improvement - That works.
5th
Cunning Strike - Replace with Coordinated Strike (When the expert uses its Helpful feature to aid an ally in attacking a creature, that target can be up to 30 feet away from the expert, and the expert can deal an extra 2d6 damage to it the next time the expert hits it with an attack roll before the end of the current turn).
Uncanny Dodge --- all good
So that'll get you started. Hell, maybe it's a five-level class, and then you either need to get some more formal adventuring skills or retire before the lifestyle catches up to you.
What I'm looking at is a variant Rogue, with a scoop of the Expert sidekick class.
So starting with Rogue . . .
Hit Dice Die D8 per Rogue level That'll work.
Saving Throws Proficiencies Dexterity and Intelligence Change to any two? Maybe even more, since the Expert is the guy who manages to survive stuff despite not having the resume?
Skill Proficiencies Choose 4: Make it any four.
Weapons Proficiencies Simple weapons and Martial weapons that have the Finesse or Light property Might just say simple weapons?
Tool Proficiencies Thieves’ Tools Change to any one tool set
Armor Training Light armor That'll work.
Class features:
1st
Expertise - Totally appropriate.
Sneak Attack - Replace with Helpful (Help action as a bonus action)
Thieves’ Cant - Or any other language
Weapon Mastery - Thematically maybe hard to justify, but maaaaaybe. Or just give them the Lucky feat?
2nd
Cunning Action - Totally appropriate
3rd
Rogue Subclass - Well here I am stumped, because developing subclassses is a hassle. Maybe just pick a feat, even if it's from the General list?
Steady Aim - Thematically iffy. Maybe something that lets them Dodge as a bonus action?
4th
Ability Score Improvement - That works.
5th
Cunning Strike - Replace with Coordinated Strike (When the expert uses its Helpful feature to aid an ally in attacking a creature, that target can be up to 30 feet away from the expert, and the expert can deal an extra 2d6 damage to it the next time the expert hits it with an attack roll before the end of the current turn).
Uncanny Dodge --- all good
So that'll get you started. Hell, maybe it's a five-level class, and then you either need to get some more formal adventuring skills or retire before the lifestyle catches up to you.