I'm sorry to hear you have being having such a negative experience with the D2000.
Can you send the output of the 'Console' tab. The error may be related to your Java Env (see this thread Fatal error: can't create ../drivers/debug/quark_d2000/obj/qm_adc.o: No such file or directory ) .
The other possibility is that there is a conflict with the 'make' being used - Do you have Cygwin or MinGW or similar UNIX-like environments in your System PATH environment?
I completely understand your frustration and we have been working on the User Experience for the D2000 Developer Kit -- An updated Version of ISSM incorporating these changes is imminent ( You can see a preview of the 'Getting Started' process here - IoT - D2000 Get Started | Intel® Software )