In general such a lateral crossgrade should be easy ... just make sure everything is tuned well when you're done. (max_connections, Tomcat threads, etc.) make sure you're in good contact with your Tam though. I would also watch out for the windows installer...In the past it has caused some bugaboos. Flawless back ups are in order. Planning how high you want to scale is also in order. Perhaps with that many iPads, you might want to consider multiple Tomcat instances with clustering/load balancing. I would also highly recommend the CJA class...The entire class is devoted to scaling the right way.
@mstenson I would be interested in hearing more of your deliberations about this cross grade. A year and a half ago we were in the same boat... singles server JSS running on an under powered VM ...let's just say we found out the hard way that we needed to scale better. I now run a five-member cluster with load balancing that covers about the same device load that you have...it was the best decision we ever made. It just required me stepping outside my comfort zone and learning a whole bunch of new skills and utilizing our existing VMware infrastructure better.
