Hi,
We have struggled with FRDM-K64 and Segger as well, we think it may be some issue with the K64 power, which is controlled by the OpenSDA uC.
What seems to be a method is:
1. Power the board, in the 2nd USB port (NOT the openSDA)
2. Power the openSDA if you want the RS232-USB
I could not explain why, but so far we think this is the way to do it..