Wow, with a glowing record like that, it's no wonder Trump wanted him for the Attorney General.
school-issued machines
Stopped reading right there. Whenever you are issued a device, you should immediately assume it's being monitored by the owner of the device. This goes for school/job/etc. The owner of the device will always be monitoring it for reasons of making sure you are using the device for intended purpose to making sure you aren't using it for illegal purposes.
"I'll know it when I see it."
I can't think of anything scarier than that when dealing with the legality of anything.
Menstruation jokes aren't funny. Period.
Each one of those (except X) has the recycling image, indicating that it's a recycle bin, not a trash bin, which is Windows.
If you want trash, you want macOS.