I had to install Windows 8 on a separate drive for work. I haven't used windows for over a decade, and now I remember why.
This is on a computer I built a couple of years ago, so no UEFI. First of all, the only way I could get Windows 8 to install was to disconnect all my other hard drives. Once I got it installed: I shut down; plugged all my drives back in; booted into LMDE; sudo update-grub; and rebooted to test grub.
Grub seems to work fine. Windows 8 is on the menu and I can select it. After I pick Windows, I get the blue windows logo on my screen followed by a message that disappears to quickly to read, (something about "your computer needs to restart now...") and I'm back to where I started at the grub menu.
I tried booting Windows through the BIOS boot menu, skipping grub altogether, and Windows goes into some kind of automatic repair mode. I shut it down, because I don't trust Windows to leave my other hard drives alone.
Seems to me to be a Windows issue, not an LMDE one, but I hoping someone else here has run across it.