I’ve attended a seminar for child protection before that was delivered by a former cop (that worked in the sex crimes division) and they said the exact same thing - in the context of correctly making the distinction between paedophile and sex offender.

Sounds like he was grooming her.

I often wonder how those people function in the real world.

Being more aware of the passage of time helps me, so setting an alarm is what I do.

If the goal is to prevent telemetry, you could use Little Snitch to blacklist all Logitech applications from being able to go online.

The scene in Horrible Bosses where Charlie Day’s character sings this song always makes me laugh.

Yep that would work.

I do sometimes wish there was a built-in save sync feature though.

I’ve needed to help a few clients with this problem. Google recently started enforcing oAuth 2.0 for their accounts. I could be wrong, but I remember reading that OS X Sierra and High Sierra don’t support oAuth 2.0, so you can’t use Apple Mail unfortunately without upgrading.

Have you considered using an alternative?

Edit: I stand corrected. App Passwords are a thing.