My assignment officer is a rock star. Seriously. She's awesome.
I sent her an email that basically said "Help! My Itinerary is evil!" and she walked me though a solution.
Turns out the program doesn't grasp that not everyone is transferring from overseas. Turns out is doesn't actually need to know where I will be on my annual leave, or how I will travel from my leave in Arlington to my consultations at Main State. Turns out, it just needs to know the things that affect the cost of me going to Estonia.
So she told me delete all that and just put in when I am flying to Estonia...and it worked! I was able to submit.
Then she told me what to look for to tell if it had gone into the great abyss (it had), and to tell her so she could get her magicians to retrieve it for her.
So theoretically, things are progressing.
Like I said, she is awesome!