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With this rule I am blending the Jack of All Trades Feature idea from Bards and the Background optional rule from the Dungeon Master’s Guide.
Familiarity with a Skill, or Tool grants the character a bonus equal to half their Proficiency bonus.
Familiarity with a Weapon, Armor, or Language gives the ability to communicate and comprehend basic everyday concepts or the ability to use or wear weapons and armor without the benefit of bonuses from Strength and Dexterity Ability Score Modifiers and with Stealth Disadvantage as well as a higher risk of exhaustion.
Familiarity represents a basic knowledge or ability that would be gained with an apprenticeship, training, or heavy exposure and use of a Skill. It basically represents completion of an apprenticeship within the purview of the Background.
A Bard with the Jack of All Trades feature can be regarded as having Familiarity with all skills, tools, languages, weapons, armor, and ability checks that the Bard can reasonably explain that they might have been exposed to during their journeys. A Bard would not be familiar with a gunpowder weapon if it was foreign to their travels but would quickly pickup the basics of a flintlock after seeing it in action or given a quick tutorial.
Each Background in the Player’s Handbook or created by the DM now only provides Proficiency in one Skill or Tool but instead provides Familiarity with any tasks that the Player can reasonably explain via their character’s history.
Gaining Familiarity in gameplay is relatively easy if during the game the PC is often engaged in activities surrounding the topic such as a Rogue impersonating a low ranking janitorial employee of a Fugger bank for a few seasons would pick up a lot of the jargon and concepts of the banking world just by exposure and overhearing conversations. The player just makes a good argument to the DM or other players depending on your style of play for why she should be familiar with a given process or tool.
A merchant’s daughter who accompanied her mother on her monthly journey to the Elven trading outpost at the borders of Qualinesti might reasonably have picked up proficiency in Elven customs, language, and writing system along with an understanding of appraisal, markup, accounting, paying tariffs, and general rules of trade. Maybe she played in the forest with elven children and learned a little about surviving in the forest or practiced with an elven composite shortbow enough to not embarrass herself with the other kids.
A squire to a knight who paid for his living by traveling from one tourney to the next across the many lands and city states of the Marches might be Familiar with Martial Weapons and Light, Medium, and Heavy Armors while picking up an understanding of how to gamble and place bets, analyze other warriors for strengths and weaknesses, a smidgeon of an half dozen languages and more dialects, a fairly comprehensive list of the Heraldry of prominent champions, fighting houses, martial orders or tourney hosts, and how to behave without embarrassing yourself around knights and lesser nobility.
With Armor the character with Familiarity must make a Constitution Saving Throw equal to the AC rating of the armor after every full minute of constant battle or 8 hours of wear while active.
D&D House Rules: