@calispike This one - the meds - could be the easier one.
If a person is on Medicare and on multiple meds (not sure of the minimum, but it is around 5) there is a service that will make daily or weekly med cards with the pills in plastic bubbles for each dose. Others make strips, labeled for day & time of day. Some independent pharmacists may offer this service. Here is one available online (not affiliated, just providing an example):
https://accupacrx.com/how-it-works/
We used a service like this for my Mom, and it was wonderful - no more arguing about whether or not she took the meds.

The second issue, whether you can communicate in advance with his doc, is yes, but how to do it depends. If he has allowed you access to his medical info, just go on the patient portal and send a message (at least 3 days ahead if you can.) You should not be charged for a "virtual appointment" or "e-visit" - just code it as a question about an upcoming appointment. Explain your concerns as concisely as you can, trying to stick to the most critical concerns.
If you do not have access, you can discretely hand a note to the person at check-in and ask for the doctor to see it before seeing him. Or once you are roomed, excuse yourself to go to the restroom and hand it to a staff member, asking that the doctor read it before coming to the room.

Do you think some of these might work for you?