This is what has me thinking it might not be worth the hassle/risk. While there's only 2 tickets for me to fuss over, it seems from the FAQ that the process to upgrade must be completed on one at a time. The link they show appears on the individual admissions. I have no doubt that in the time it takes to go through one, they will all be sold out. So, if you are lucky enough to land one for yourself, odds are everyone that's going with you will be out of luck. It would make a fun vacation much less so if that vip badge meant spending most of the events separated.
To add to that, based on the initial mess, I can imagine a worst case scenario where you lose the tickets you have in the process of upgrading since its technically a transfer. Not worth it, I think. Bird in hand and all that...