I have performed the steps you explained, then modified the debug sessions to not execute the target initialization script and not load the .elf into memory. This is because i would like to attach to my 32 bit code which is already running on the target. From this point i tried setting the pointing the gdb to:
1- CW ARMv8 gdb: it attaches and correctly identifies the architecture of the processor as an arm (aarch32). However It is not able to follow the program counter, breakpoints do not work, it can't step, not even from the debugger console (stepi), and the command "info registers" has too few registers to provide an understanding of the situation. In addition it does not account for the MMU being enabled and both the Memory Browser and Disassembler point to the physical addresses instead of the virtual ones, clearly missing the real location of the code and variables.
2- CW ARMv7 gdb: still have the same error complaining about python missing and debug does not start.