You just don't know how to use iTunes. I used to be in your boat. Once you learn you'll realize it's a lot easier than you thought. I can delete my entire library right now and add it all back with the click of a button.
Apple actually made transferring music not only easy, but beneficial. As I said, I can delete my whole library and add it back in my sleep. The problem is, it's not what you're used to. If you play PlayStation your whole life you'll probably look at an XBox controller cross-eyed. That doesn't mean it's unusable by any means. It just means you don't know how to use it.
iTunes is a pain in the ass if you don't know what you're doing but it can be a breeze if you do.