I'm not a Mac fanboy, but I think you'd really have a problem finding something better than the Ipod Touch. It's not the most durable thing in the world, but if you don't drop it......... I haven't managed to kill my iphone 3G in three years.
You can bitch about Apple reliability, but they still have better customer satisfaction than anyone else.
Ipads, iphones and iTouches.... people I know love em'
If you wanted a phone too.... you probably couldn't go too wrong with the Galaxy Nexus.
The Android Winamp is pretty good.
I pretty much don't sync, usually don't use Winamp unless I want the visual goodies. Winamp is on my main desktop with my music, but I usually use Google Play and sync that. Leaves room for movies and apps on my Android tablet (a rooted Kindle), my iphone and any of my 3 computers.
Global Movies and TV
God grant me the serenity to accept the things I cannot change; courage to change the things I can; and wisdom to hide the bodies of people who pissed me off.