I feel like the first half of this advice would fit friends or housemates better than a boss-employee relationship. Carol hired LW so she doesn't have to think. LW is an indulgence Carol can afford by being rich. If LW tries to make Carol think Carol may respond by getting rid of the thing bothering her to think, i.e., LW.

I'm sure Carol is kind but will she be kind when it causes her inconvenience? Especially the recurring inconvenience of having to think about how much she spends on food?

If I were LW I would quietly make arrangements with a food bank, and ask if the pickups can be done with the best looking car available.

(Also, LW, I'm sorry this part of your job is boring, but well, it's a job.)