What's a good metric for when to stop masking?

Regular cloth masks help prevent you from infecting others, but have only a very small protective effect on you. N95 or KN95 masks, used correctly (which includes using them for only one day each) have a very strong effect at preventing you from infecting others, and also give a significant (but not total) protective effect from you. N95 masks worn for more than a day are basically just cloth masks.

But to the OP, the easy answer is to trust the professionals. If you think your situation is sufficiently different from normal that the general CDC guidelines aren’t good enough, due to the vulnerable family members, then ask their doctors for advice.