Soldato
I've never had a problem with iTunes...
OP hates iTunes... OP doesn't use another program to eliminate hate = FAIL.
Why should he though? It's the software designed by the maker of the items he's paid for. Most of the decent tools that can do this as well either charge or put in cripple-ware which deliberately slows the transfers down or adding a conversion wait time (even though nothings being converted).
I've had problems in the past and I absolutely hate the UI for it. My wifes old is a nightmare to transfer stuff to where as the company iPhone I have is a lot better but still not brilliant. I still hate how you can't actually use it as a storage device and drag and drop items to and from it.
M.
Generally, iTunes is ridiculously easy to use.
Just need to make sure the files are where it thinks they are (just like any other media player with a library....)