Hello Nolman,
Please go to:
http://forum.behringer.com/showthrea...ghlight=REAPER
around post#24 you'll find exchanges with Nick Davis who also had issues with a Win8 64bits system. I understand he solved the situation in installing the 32bits version of cygwin.dll; I believe Win7 also has a 32bit applications section too.
There seems to be some incompatibilities between 64 and 32 bits versions of cygwin (one not being able to run applications referencing the other).
I may end up porting everything to mingw if cygwin is such a hassle, although it makes porting much easier from linux to Windows!
Hope this helps, let me know.
-Patrick