My aunt has an older dog who has diabetis. I don't know if going frequently is a symptom in dogs as it is in people, but if so, that might be something that should be checked out. Even though older dogs can't hold it as long, this sounds like something more than old age. I agree with Logan on dealing with the vet. Also that Bil-Jac sounds like a good method for the pills. I used Snausages with the same method. You can mold them around the pill.

HowieDawn, did you get the puppy for your Grandma?