Has switching to iOS been a challenge at all for you either on the device front or media wise?
No, anything but. One of the major reasons that I switched was because of media playback - my cars will connect via USB to iOS devices, bit only via Bluetooth for Android, and whenever I entered the car it was a coin flip if the thing would continue playing where I left off last. Press the play button if it played nothing - nothing happened, so I had to fiddle with the phone (thankfully I could "OK Google Now, open Play Music" to at least voice start the app) to get anything playing. The iPhone is perfect, I have a bunch of headphones with inline music controls and they all work with the iPhone (and did not with the Droid Maxx - they did at first, but something blew out and there is no Motorola store to go to to get it fixed, so I was using BT earbuds with the same problem the car stereo had.)
My Android home screen was pretty simple, just two screens with two widgets (one was the VZW one with the amount of data used, the other was a clock/weather with the battery %, because Google decided against showing that on the status bar - moronic.) iOS now has widgets in the notification shade - not as sophisticated as Android, but more than good enough for me.
The fingerprint unlock is fantastic, and of course the camera is as well.
I've had an iPad for 3 years, so it wasn't a huge transition. Plus my wife and kids all have iPhones, plus my siblings and even my Mom, and my wife's siblings and their spouses and kids (except one person with an old Razr Maxx HD.) That's 28 iPhones and 2 Android phones in the extended family. I also have a Macbook and an iMac, so going iPhone was just overdue.
To be honest, I only bought Android at first 6 years ago because Verizon didn't have it, and then, when they did, it was the stupid glass backed iPhone 4 and then 4s. When I bought the Maxx two years ago I decided to stay with Android one more time (rather than get the 5 or the 5s) because of the large battery on the Maxx (I live in a place with weak mobile signals, so the battery was important) and the promise of rapid Android updates by the Google-owned Motorola team. Well, as I said, the battery life on the Maxx has been a disappointment, and the Motorola support - a buggy KitKat build that took six months to update, plus the crappy Lollipop upgrade timing - has been a letdown.
Maybe I'll feel differently in a couple of years, but right now, with the crap job Google did on Lollipop (a memory leak that still persists? Stagefright bugs that stay unpatched for months?), and Motorola's crap support of their phones over the last year, I want them (Google - I'm done with Moto) to prove again to me that Android is worth switching back to. I hope they can manage it.