I have two PowerEdge 610s with Server 2008 R2 on them. They both exhibit the same problem when trying to upgrade to 2012 R2: I click next to the initial splash screen, it says that setup is copying files, then it briefly flashes "Setup is starting" and kicks me out. No errors are logged anywhere that I can find. Some research suggests that the 100MB System Reserved partition may be the issue -- 2012 R2 requires 350 MB -- so I moved it to C:. After that, I could see it creating the $Windows.BT folder into which it copies its bootloader, but it still crashes. I then moved it to a driveletter-free partition of 650MB, just in case it wanted a different partition.
I already wiped the one server and installed the OS but the other is a hyper-v machine with a number of servers. The amount of data is too large for me to copy right now. Anyone run into this before?