I hear you homie. I use to jailbreak my phone all the time. Until recently ios6 was updated i had no jb so i just said fukk it. Made yhe switch and been happier ever sense.
I use playerpro and isyncr and the shyt been good money. Plus i love that i could unzip a new album/mixtape and add it instantly to my phone. No need for cpu.
i don't really listen to music on my PC its all really done on the MP3 player. Android doesn't keep track of all that data last i checked. the iPhone keeps track of and adjust all that metadata.
i do miss the ability to extract music on the fly though. i feel like Android is the better cell phone overall but the iPhone manages your music better.
i'm not really loyal to Apple though. more than likely i'll end up back with Android. when we get LTE here i already know the iPhone 5 won't do voice and data at the same time with Sprint. that might bring me back.
you are a casual user. All these issues can be fixed by simply looking around.
i see this Proplayer that seems to do what i like but i'm not the type that's gonna look for all that sort of stuff. i don't wanna root or jailbreak my phones. i wanna take them out of the box and use them as is basically. i'm still looking for a way to use a Nike+ sensor with Android too.