Woooooooo! How exciting to put the plans into print!!!! I think they are looking really good. At first I was concerned about YOU, but you mentioned your insomnia (been there, ugh!), and it sounds like you've learned to make it work for you and your family - so go girl!
As for Gavin's meds - any of the Disney resorts should be able to put them directly into a fridge for you, even if your room isn't ready. They are very, very good about this. We have had groceries delivered before too and they will store them - so meds, no problem! Disney is so good about this kind of stuff!
As for plans on Day 1, I vote DTD. It will be fun, yet relaxing. It's DISNEY, but you don't need to use a park ticket. Plus, you are still on property, so it's easy to get to your Chef Mickey's ADR. And btw, FANTASTIC way to kick it off with CM and a monorail ride! Your kiddos will love them both. (and you will too!)
Prize for best planner/least selfish woman - YOU!