Turns out after creating a new board, modifying firmware & hours debugging hardware, firmware, and mac os, the issue was due to (Karabiner)[https://github.com/tekezo/Karabiner-Elements/issues/1828] and mac os clashing on keyboard control and not the Kinesis BLE's fault at all.
I've since removed Karabiner and have fixed the issue completely.
I suppose it wasn't a total waste of time, the debugging revealed that at the previous setting of 7ms delay, I could potentially run into key chatter if I type at upwards of what I assume to be 300wpm+ (me smashing keys as fast as I can). This is something I can't replicate at 2ms delay so I'll stick with 2ms delay and loop debouncing 3 times for now, depending on actual battery life (expecting a drop from 6 to 2+ months).
Diving back into the firmware also let me fix a bug that resulted in inconsistent rest timer alerts.