Me too, I have had mp3 player that requires some weird bundle software to sync(an mpio with 64mb of memory...yes, 64mb) at usb 1.1 speed:bigeyes: Probably 10years old and still working. I have had mp3 players that you just drag and drop the files into the sd card. Also had players that you just drag and drop the file through usb.
After trying everything, itunes is still the one I prefer. The word "sync" sounds complicated, but it really isn't. It is nothing more than putting a tick beside the playlist that you want to add, then click the button sync. If there is any new songs in one of the playlists that you originally have in your i-whatever device, then the new songs will be added automatically when you click the sync button. Can also help to manage and backup your apps.
Of course, I do agree that if you only use itunes for sync and not for playing songs, then it might be a big hassle to manually add it to itunes, create playlist, then sync. Coz when I first started using itunes, I only used it for adding mp3 to phone, then it was so so so troublesome. However, once I started managing the albums and playlist on my workstation using itunes, it became very simple to add or remove mp3. This is because in the first place, I already have the playlist that I added for the workstation.
Oh and I am not a apple fan. Hate mac.