Regarding iTunes. I’m not the guy to ask about iTunes if you’re looking for alternatives!
I began messing with .mp3’s and digital music in the 1990’s and have tried a lot of music managers with plenty of tedious frustration resulting. When I came across iTunes my experience was just like the late Mr. Jobs stated, “It’s like giving a glass of ice water to somebody in **bleep**"…
I’ve been using iTunes since 2004, and my sister also uses it extensively. So I recommend nothing but iTunes.
In conversation with others about digital music management, I often hear good things about Media Monkey and WinAmp. These have been around a long time too and may be better suited for you than iTunes is… You’ll have to see for yourself.
