My hassle is usually: Where do I dig up that keyboard and spare HDMI video source to bootstrap the Pi. Currently the MAME cabinet does that well, but not everyone has a MAME cabinet.
I’ve had this problem multiple times and find this approach really nice (and wish it shipped with raspbian!)
Edit: forgive me, I see that's not what you meant at all. Or maybe it was? Either way, the point is valid.