Nexus 5 is all the phone one needs, at half the price.
I'm still getting the 6 Plus instead of the Note 4 though.. simply because it's three fewer weeks to wait ;-P
With movies you're SOL, but Google Play literally let me just upload my iTunes music folder, and aside from a couple of metadata glitches, it just worked.
Step 1. Install Google's Music Manager on a PA which also has you iTunes library. Step 2. Let the automatic sync run.
Not exactly painful. Potentially time consuming with a large library, but virtually none of it is active time.
If you "bought" your music with Apple DRM, you can pay another fee to actually own it and be able to play it on a non-Apple devices.
If you "bought" your videos with Apple DRM, consider it a lesson learned.
There's no "lesson" when I have made the conscious decision to stick with Apple all these years. I may have paid a premium paying for iPods and iPhones, but I feel my time is valuable enough to not have to mess around with my media files in any way you describe. Nor do I feel the urge to spend money on music I have already purchased, but I don't see that as being a mistake from which to learn a lesson. Nothing has happened to me with Apple or its products so egregious to feel compelled to take on anything like you describe.
Most people make the mistake to think they 'bought' a movie or DRMed music file when they really just rent/lease it long term.. And then they realize they're screwed when they want to the freedom to buy whatever device they want and have 'their' music they 'bought' on it. After all, most people didn't grow up buying a CD from Best Buy and having it work on their Best Buy CD player but not on their Sony CD player.
You may have realized what you bought into and consciously made the decision that you accepted the limitation in rights/etc in exchange for convenience/etc, but most average consumers do not.