-The Apple Rep - Said in order to hack, they must hack Apple, so to speak. DID say it's possible to get malware, BUT the only place it could reside would be in your Safari history, clean that and there's nowhere for it to go.
-The VPN deal, There are various services that, for $2.99 or $3.99 a month, provide you with multiple IP addresses, guessing like the public library, sanitation department, so you don't have to use your now exposed address. It DOES slow internet speed. I briefly looked at one service, just a couple dollars per month, gives you Ten numbers and instructs to plug in to VPN section in options. From what I read journalists are big consumers of it, however, so are criminals.
-15 years Marine Corps/Army, tech is not my specialty, Jailbreak is a football play to me, have heard of it and read do NOT pursue it. Email is the gate inside I'll wager, from there photos, options, book/music, Safari all was brought up. Skwirk.com was brought up, signed into by a teacher, and numerals show.
-Tests were more like capability, speed, accuracy, etc. i.e. At any given moment I'm bringing up a fresh draft in email I'm curious you can get there and stop me. Less than 5 seconds every time. Restrictions w/ passcode. I "allow changes" under accounts to open mail options, select S/MIME. Not mention it... time passes I'm informed what I did and S/MIME is no longer selected. Things like that, Checking capabilities. Line, Skype, Viber (100 contacts kept while deployed) those apps they cannot touch. The actual passcode into restrictions cannot be read or changed, contacts I shut off and couldn't be turned on, there are things out of reach. Which beats Windows and Google/YouTube by miles. After realizing I was out skilled, I sat back and took screenshots. Told him any bank/financial nonsense, there's an FBI field office in Pakistan. Nothing like that occurred, just trespassing and ruined something in c:\ on my desktop. Hit with a virus 4 times called Shootsama. Can't find a thing on it, have screenshots, it pops up and informs you it's now uploaded and is in your add-ons or extensions in Internet options. Delete it and it hits recycle bin and bounces back. My error on that, got it from mail, Facebook, messenger apps, point being answering from people I didn't know very well. 250-300 people from the region on your list, makes it easy. That list has been consolidated.