Joining in! I've never read a PTR before, but I saw a fellow Minnesotan on the boards and had to check out your plans!
First of all, I have several pics of myself at WDW in the 90s wearing shortalls, so it was fun to laugh along with all of you at our previous wardrobe disasters.
When planning our December '09 trip it was all about reducing wait times - so here's a few tips on the characters:
You may already know this, but ToonTown usually opens 1 hour after rope drop. They do another little rope drop at the entrance to Toon Town an hour after the park opens. (You can confirm this when you arrive, but from what I understand it's common practice.) So, you can do some Fantasyland attractions during the first hour then head over to ToonTown. If you're at ToonTown Rope Drop you will be able to get right in with the princesses and if you're in the first group possibly even get pics with more then one of them at a time.
I've heard if you head to Character Connection at Epcot (and/or Camp Minnie Mickey in AK) at Rope Drop you have the chance of getting a photo with multiple characters as well. I like your idea of sending one of your party to get Soarin fastpasses while the rest of you head to the Character Connection.
We found the lines for Buzz and Woody at MK to be much shorter then at DHS. The down side is you don't see them together at MK. Buzz is in Tomorrowland and Woody is with Jessie in Frontierland. We waited about 5 minutes for Buzz and 15 for Woody at MK. The next day at DHS the line for Buzz and Woody by TSM was over an hour!

And we were there at an off-peak time of the year. (early December)
Your plans look great. I hope you all have a great time! Less than a month now . . . Congratulations!