I was having no trouble with KDS/KDSK in terms of compiling and now it's being touchy, running less and less consistently now to a point where I can't get my application on to the chip, and if I open terminal I'm seeing the last program that was loaded onto it running. I tried unplugging, holding reset while plugging back in and reloading OPENSDA 2.1 multiple times, and while the board automatically resets and appears as the J-Link under COM Ports, it won't load code. It won't even load a file with just while(1) or for(;;) and no code, no includes other than things like studio.h, etc...it will however load example projects. I don't understand this inconsistency - I had this working for almost a month and in the last 24 hours it started to do this.
Is this what you are getting?

Not sure if this will help at all because you don't say anything about Freedom, but there are a few links already started related KDS/K22, and the KDS platform/debugging in general that may help you:
FRDM-K22F: Debugging with P&E OpenSDAv2.1 Firmware
Re: First impression with KDS 1.1.0 Can't Debug FRDM-K64F with OpenOCD/CMSIS-DAP
Using FRDM-K64F with P&E and Segger OpenSDAv2 Firmware