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Thats it.
Steward is my second highest skill only surpassed by trading.
If it doesnt go up just from the title then you need to start getting income.
The skill passively levels. A captain is responsible for Feeding and paying an Army, which is Stewarding.
Edit: I just realized this thread is from 2020, the game has been updated since than.
All you need is... Make sure you have every type of food, and let time pass.
You don't need to make yourself quartermaster, as long as no one is assigned as one. As you cover all unassigned slots yourself.