I tried iTunes back in 2009 when I was trying to get some music off of an iPod. Worst user experience ever. When you have to watch 5 minute video tutorials on Youtube to figure out how to do something, your user interface probably sucks.
Also, yes, the bloat and the constant updates to support the bloat.
You put music on your iPod or your remove it. It's not meant to bring around to your friends house and take all the music off of it and onto his computer. This is by design.
Also, yes, the bloat and the constant updates to support the bloat.