Re: Polaroids FTW
"keeps nude pictures of themself anywhere"
You're assuming they deliberately kept the pics. They could have taken them for a laugh one evening with their partner, and then deleted them immediately, but they auto-synced to iCloud before they were deleted.
If they're not tech savvy, they may not have realised the significance of their iCloud/photo stream setup. I've seen very tech-savvy people make mistakes with similar things like dropbox.
Edit: Also. Cloud storage providers will often recover deleted files for you if you ask them. Even if they're gone from the trash folder in your cloud drive. I know Box do, and it's an infuriating risk when I'm trying to keep data secure on their service.