Should I wear a grounded ESD strap when probing/debugging my raw boards?
My entire office is carpeted, and we constantly debug/test raw PCBAs at our desks. I take care to ground myself on metal objects around me, and I have an ESD mat on my desk. When I have to transport boards, I put them in ESD bags. I also take care to ground myself after getting up from my chair, or upon sitting down. When passing off boards to others, we always do the "EE's handshake", where we touch hands before exchanging the PCBAs.

This has worked well for us, and I have yet to see a PCBA damaged due to unintentional ESD.