Hi there! New to your report but wanted to stop and say hi. I'm a surprise planning lover myself (hate surprises for me but LOVE planning them!!).
I totally agree with staying with your plan about surprising him while you're at Disney with everything. Trust me, as a surprise planner, you can explain anything! If he finds something in the suitcase he doesn't like, he can do the packing for the entire family.
Let me think on a way to share the hotel surprise! I know you can get those calls from Mickey on line-that might be a cool idea. Also, we're going in December. I would totally send your family a post card (from Mickey and gang) telling them they've been "upgraded" to a WL stay!
I'm working on some surprises for our upcoming trips in Sept and Dec-check out my PTR if you want some ideas.
Also, Betsy (a fellow dis'er) does wonderful baskets-you can send her the stuff (no food) and she'll do the basket for you. That's what I doing so I don't have to worry about hauling anything with me and getting into the room for a suprise. Very reasonably priced and she doesn't mark up the park merchandise that you put in your basket!

there are pictures of my baskets for Sept in my PTR if you want to check them out. Betsy also helped with the disbotique and Creative DISigns board Big Give.
Happy Trip Planning! I'm having a very hard time keeping my mouth closed with all of the surprises! Thank goodness for the DIS boards or I would have blown it long before now!