Michele,
If he has a Blackberry, does he use Outlook for his email and calendaring? If so, you can scheduling tasks for him, and you can make them repeat. He will get notices that the task is due in 15 minutes, past due, etc.
Feeding before bed: Lucy expects this too. My compromise has been to give her something with virtually no carbs or bulk. Fortunately, she loves nutritional yeast and bonito flakes. So before bed she gets a tablespoon of nutr. yeast and a small sprinkle of bonito flakes. No carbs thus no food spike.
One other thought: Has Molly ever been tested for hyperthyroidism? Has she had her blood pressure tested?