I cannot imagine how on earth anyone could have trouble with iTunes. It is completely idiot proof.
I have 5 different music libraries comprising just a tad over 3 TB spread over a laptop and two portable hard drives.
I use 5 different iPods plus my phone. The music is sorted by genre, artist, album, era, etc.
All of it managed and synced with iTunes and it could not possibly be easier to use or to find exactly what I am looking for, when I am looking for it.
I see threads like this and really wonder how on earth anyone could find iTunes difficult to use.
I do this and have zero problems with iTunes. My primary complaint is that they keep messing with the interface and I have to relearn where buttons live.
There's nothing better than an Orangina after cheating death with Digger.