list of suspects
So - long time-frame, multiple devices, multiple O/S and quite a small group of prime clickbait.
1. was it a "free WiFi" access point at the Emmy or Oscar awards ?
2. someone in the NSA cloud monitoring team just got his prize swag stash onto a USB stick and out of the building ?
3. it really was that simple password vulnerability on the "find my iPhone app" plus said celebs moving photos from other sources to their icloud (or getting them sent from people with other devices) ?
4. a cynical attempt to either sell a security service or discredit Apple ?
just my very non comprehensive list, any better suspects ? but please remember "Investigating or commenting on any high profile leak is like trying to hug a hedgehog, the harder you try the more pricks you encounter" and I'm just the first....