Getting music on an ipod was always a pain unless you bought the music on itunes or ripped a music CD directly with itunes (yes, that was an actual feature. hard to imagine these days).

No simple drag and drop onto a mounted USB drive like all other mp3 players back in the day. Maybe more of a lock-in attempt instead of lock down, but related imo.

"locked down" is a vague, moving target. The criticisms of pre-OSX MacOS was that it was an operating system for little babies, and not serious tech enthusiasts and power users. Also they were too expensive, and you can build a PC that is 100000x more powerful for cheaper. This literally hasn't changed.

Their previous lock-downs were on the hardware level, not offering ISA slots and stuff. The original Mac (then Mac+ and classic) had no expansion slots at all, and they started adding them only later.

First iPhone was 18 years ago, but yeah it around the time of the first iPhone. IIRC he actually mentioned that because he had already been confronted to Apple’s lockdown before the iPhone. It was a long time ago and I was young, so I don’t remember the details.

There was a decade between them.