With Microsoft's impending end-of-life support for Windows 2003 and all the recent SSL attacks, it looks like moving to SHA-2, TLS1.x, etc. is inevitable. I've previously had an impossible time getting Dragonpay to work correctly on Windows 2008 R2 64-bit at Softlayer. But this time around, when I had the OS reloaded for Windows 2012 64-bit, it was surprisingly smooth. Granted that it took a little bit of getting used to the new interface, but it wasn't that much different from Windows 2008.
Figuring out where to find the SMTP service took a bit more of a challenge but I found this incredible and very detailed step-by-step guide that worked perfectly: