I imagine an expanded story, based purely on speculation. Old guy comes into the store and buys a new iMac. This guy recognizes him as a neighbour or friend-of-friend and comes over to say hi while another Apple sales associate is checking him out. He overhears the sales associate mention Apple's free program to transfer data. The old guy says "nah, I don't want to leave my computer here" and the friendly guy says "hey, no problem, I'll just pop by your place later and do it for you at your house". The original sales associate might have thought that was a conflict of interest so he reports it to a manager.

Now the manager is in a tough spot. This is some kind of official internal complaint and it is literally his job and his duty to investigate. He talks to the employee and the employee confirms the report. It's now out of his hands, has to go up a chain to a regional manager. It gets passed around a bit until someone unfamiliar with the employee looks at the policies and facts of the matter and they make a by-the-book call.

I can totally understand the frustration. It reminds me of some kind of Kafkaesque nightmare where justice is run through an algorithm. At some point we'd all hope a compassionate judge would look over the human's involved in the situation and apply some magnanimity.

Each person in a chain had an option to use their judgement to break the chain but nobody did. This isn't an indictment of Apple as some may want to see it. It seems more likely it is a pretty standard outcome of people following a bureaucratic process.