Hi Jen,
I'm joining late but at least while this is still a PRE-TR! I've read some of your other TRs and they're so fun, so I had to read here too.

A bunch of random thoughts on previous posts:
LOVE the outfits, especially the newest pink one.

Wish I were in shape to wear any of them. Passed on that Old Navy Groupon - DARN!

I like the blue & white striped one for Yachtsman - seems in keeping with the theme! Also love the shoes for your anniversary dress.
Your Disney drawer looks like my DVC bag (the freebie we got when we joined) it's full of lots of the same things - including those Mickey BandAids!
On your videos, how about the top 5 cueing areas?

I think I read that they re-did the one for the Pooh ride, and of course the HM, and lots of them are really fun and might reassure people that even waiting in line can be entertaining!
Also wanted to say I do the same thing with a chart for our itinerary.

You really should experiment with Excel - I think you would like it -- I'm a major list-maker too and Excel is great for ranking/sorting/reordering, etc.
Someday we may drive. Going down I think would be fine, but it's the coming back home that makes me cringe.

Have you thought about finding some good books on CD from your library to keep you awake/alert? That might be good to help pass the time, too.
Don't stress about packing - you already have all those outfits and the drawer stuff set aside, so you're in great shape! Getting a DH packed is another story.

I always ask mine to get his own stuff together and he's good about it - I have myself and the 3 girls to get together, so that's plenty! I really don't have any advice on this point, but wish you good luck & hope he's feeling better (at least you aren't flying with the potential ear issues - that could be bad news).
I can't remember whatever else I was going to chime in with. We're doing a 2-way split stay for our first ever as DVC owners in August and are really excited. I hope you enjoy the 3-way split! Would it be a total pain to pack for that first night in its own bag? Might make things easier when you're down there - just bring that one bag in with you for the night? Just a thought.
Have a great time - almost there!!!