I had an iphone 2 and got fed up with iTunes so switched to WM6.5 4 years ago I think and had an ipad 2 that I sold after the Surface RT came out the sale of which paid for a sizeable chunk of the RT so yes all my media is fairly recent.
I can see where your coming from and losing all the media you have purchased over the years would be hard to let go. If you add up the investment you've put into apple then you have to justify switching and starting again. Ive had people ask me about switching to windows that like yourself are firmly entrenched in apple and I can never recommend to them to make the switch its just not economically viable. When I switched I probably had to swallow about ?150 loss in apps and media. For some people that figure can easily hit ?1000 over the course of five to six years use and its just not worth the loss. Its not a case of whether apple do things better or whether blue fixes all ills. You've got to ask yourself what works for you and if the investment you have made is worthwhile. If its apple then stay with apple, android stay with android. For me MS ecosystem works great and the investment Ive made outweighs the investment I lost.
The thing is the majority of media we own is only rented and isn't actually ours no matter what ecosystem you think is best for you.