I was wondering about dropping back to 1.0.1 (I'm running 1.0.2) to see if that makes a difference.
I'm not using the Oak sleep and wake functionality, I'm using an external reset line from an STM8S. The signal looks reasonable on the scope. Drops to a few millivolts, not spot on ground but close. Pulse looks to be wide enough, I believe that 100us is the minimum, I went for 300us to be on the safe side. The Oak sends the usual garbage characters to the serial port so I think it has at least started the reset process. It just gets to a point where it occasionally just hangs just after the garbage appears on the serial stream.
Regards,
Mark