I bought a Zune 120 about a month ago and I love it. It has a option to set the folder you want it to sync to. So anything in that folder syncs with it when plugged in. If you want to remove something, remove it from that folder. It does not even have to be plugged in to sync because it's wireless. It also plays WMA files and I have a ton of them.
That iPod problem is pretty common. Drag and drop is the only way to go. I would flash that old iPod with Rockbox firmware and then you can drag and drop directly to the iPod. They just released a major upgrade change to their firmware so I would try it out. It's pretty easy to remove too if you don't like it.
http://www.rockbox.org/download/