I've been using iTunes (and the Music app) since it was released, and I've always loved it, but I've somehow never really made the most of it in all that time. Like so many things, I know there are a million things to learn and discover with this tool, and if I only had infinite time, I'm sure I could find more of them.
One thing I'd always struggled with is new music: there are so many great albums I've never listened to, and so many new artists all the time, and yet a lot of the time, making a purposeful effort to listen to new music never worked very well: I didn't have the free time I had as a kid, and listening to something new while doing something else didn't let me really hear the new music well, and most of all, hearing an entire new album at once was too much novelty for the mood of my brain these days: I needed some familiar songs as well. I love hearing songs I love, and I don't get enough time to listen to familiar songs, either, these days.
Finally, a few months ago, it occurred to me to create a Familiar playlist and an Unfamiliar playlist, and mix those:
My Familiar playlist has songs I know and love - hit singles (the good ones) from the years I listened to the radio the most, and several dozen albums I know well and love from artists I know and love: Sinead O'Connor, Shawn Colvin, Rickie Lee Jones, Queen, Kevin Gilbert, k.d. lang, Joni Mitchell.
My Unfamiliar playlist has artists and albums I'm not yet familiar with, but want to listen to: Karine Polwart, The Roches, Joanna Newsom. It includes newer albums by bands I've loved but haven't kept up with (Heart, Elvis Costello - he's put out SO many albums, it's hard to keep up).
I created those two playlists by dragging specific songs and albums into regular playlists, and then I created a smart playlist called "Familiar and Unfamiliar," which randomly mixes tracks from those two playlists, and excludes anything I've heard recently.
So now it's like having my own personal radio station - I hear lots of my favorite songs, but I also hear new music mixed in with music I already love. It's been wonderful to discover songs I hadn't heard ... and my brain doesn't get overloaded with new stuff, since there's plenty of the familiar as well.
I've picked up so many fantastic CDs at library sales over the years, and it's truly a joy to get to discover them all at last.