Stewards, butlers, maids, governesses, custodians, and groundskeepers. Caretakers are people who directly care for the things which elite institutions and noble families value the most. Depending on the wealth of the family or the size of the estate, it may require the supervision of several custodians in specialized roles to get all the work done. There is a certain autonomy granted to caretakers, who are entrusted with taking the responsibility entirely from the hands of their employers. The best caretakers are hardly seen or heard at all, making them privy to all manner of information their employer trusts to remain confidential.
Did you serve a wealthy family, or did you serve an institution (such as a castle or private school)? Are you still beholden to these loyalties, or are you estranged (or even ostracized) from your previous role?
Ability Score Increases: +1 to Wisdom and one other ability score.
Skill Proficiencies: Two from Culture, Engineering, Insight, Intimidation, Nature, or Stealth.
Tool Proficiencies: Any two of your choice.
Suggested Equipment (Cost 15 gold): Fine clothes.
Feature: Live to Serve. While in a settlement where there are castles or other estates of the nobility, if you have not made yourself unpopular in the community, you can ply your trade as housekeeping or groundskeeping staff. This supports you at a modest lifestyle. While plying your trade in this way, you can Gather Information simultaneously at no penalty. After serving at a given establishment for at least a week, you gain an expertise die on checks related to navigating and recalling lore about that establishment.
Adventures and Advancement. After enough adventures, you become recognized as a superior housekeeper or groundskeeper. Whether you are an independent caretaker or one associated with a specific family or institution, you gain the service of 4 novice caretakers under your supervision. Certain nobles are in such need for somebody they can truly trust that certain caretakers are able to find lifelong employment.
Connection and Memento. Roll 1d10, choose, or make up your own.