I did something like this as a day trip last year. Alas, I just received a "save the date" card for my nephew's wedding, which will be the week before. Can't do both, even flying MDW to SMF for $133 each way.
My buddy and I, also part of the GtG volunteer crew, booked our hotel back in liek September. We decided it was just easier than trying to deal with the whole lottery thing. We don't mind walking to and from the con center. It's a good way to wake up in the morning!