I use three pillboxes. One has 28 boxes, that i fill once a month, and i take all at night.

My 2nd pillbox has my diabetic metformin in it, 7 slots, that i put 4 pills in each slot, and i use 2 pills a day, so it lasts me 2 weeks. But its easy to verify i take 2 pills a day with meals, altho sometimes i forget.

My 3rd pillbox has 2 slots, i take 1 pill every other day, its a diuretic. The 2nd slot is for a potassium supplement which i am supposed to take with the first pill, but i have been skipping lately. I keep track of what days to take it on my phone calendar. Sometimes i skip a day, sometimes i take it 2 days in a row, and i alter the calendar accordingly. It goes out for like 3 months. I dont remember otherwise.

Then my insulin is in a separate old makeup bag, and my glucose monitor is in another.

I have 2 small suitcases, one for daily and glucose meds, and the other for the monthly meds.

I try to make it as small a hassle as possible on me.