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Often people who live in supervised situations will ask family members to secretly purchase OTC medications that they probably should not be using. These are often things like laxatives which everyone knows that overuse will have disastrous results.
However people in assisted living may still be relatively competent and resent having their usual habits curtailed.
The most dangerous action is taking OTC meds that interact with prescribed meds, for example using aspirin with blood thinners.
Without knowing just what Grandpa is doing it is not possible to give positive advice and decide whether to turn a blind eye or come down like a ton of bricks
Usually in Assisted Living, all prescription medicines for a resident is locked in the nurses office, and only the Med Tech can give the resident their medicine. I know my Dad couldn't even have an aspirin bottle in his room, that is how strict the facility was, and for good reason.
Sorry to hear your dad is depressed about being in assisted living and is trying to self medicate. I know its not easy. No one likes change.
Can the Assisted Living staff help your dad with counseling? family therapist? social worker? or joining a support group?
My dad was also very stubborn. He lived at home till he passed at the hospital. Sometimes I tried and tried and there was nothing I could do to change his mind. I do regret not doing more still. It something that weighs on me.
Please try and see what resources might help your dad cope with this new stage of his life.