With the example of the charger-on-the-bottom, where does the break down come from?

Was this never even considered an issue? As in, did it just never get considered as something bad? Did it never get focus grouped in a wide enough range of users for someone to question this? Was it noticed, questioned, decided it was works as intended?

It just seems like with a company the size of Apple who all work under draconian NDAs, why not have an internal employee focus group? Hubris of the design silos?