Sorry to say this, but I learned a long tme ago that Apples and Oranges are NOT the same fruit - LITERALLY (with Windows being Oranges in my analogy). Apple is made for, well, Apple. Personal opinion, but I won't touch Apple product - just too "exclusive" for their own good.
So, when we bough a tablet for our child, we bought a Toshiba with Android system. It's got USB, HDMI etc etc. I plug it into the laptop or the desktop, and it syncs and downloads everything without a problem. All the issues supposedly with Android proxies are GONE - I never even had a problem as there was a SIMPLE way to get around it (that I had to show the tech guys at our local Uni so they could themselves put a user guide for Android users up
)
Anyway, sorry, but I have NO good advice, except if you have Apple, stay with Apple stuff, as a LOT of it just won't talk to other systems at all, and even within their own OS I have heard of issues. The lack of USB (unless that has changed) is a REAL hindrance for Apple, and I ave heard the workaround cable is LESS than adequate.