This is how I handle music.
For a long time, I bought CDs, and after that, albums and songs through iTunes. Last year I switched over to Spotify premium. It costs ten bucks a month and you can listen to as much music as you want. It doesn’t have every song in the world — it’s missing the Beatles catalog; Taylor Swift, famously; and odd things, like that Hootie and Blowfish album — but it’s pretty comprehensive.
I use the Spotify app on my Windows desktop computer at work. I feel like this app is a bit of a resource hog, but it does the job.
Generally, when I find a song I like, I click the check mark next to it to save it to “My Music”. Then when I’m feeling like listening to music, I go to my list of songs and just play at random. This means I usually get a really crazy mix of songs. For example, the songs playing as I’m writing this are Victory, by the Walkmen; I Get Around, by 2Pac; The Naming of Things, by Andrew Bird; Believe Me, by Lil Wayne and Drake; Can’t Find My Way Home, by Blind Faith; In Summer from the Frozen soundtrack; The Next Movement by the Roots; Girl, by Beck; A Tale of 2 Citiez by J. Cole; Hurricane, by Bob Dylan; and Barry Bonds, by Kanye West and Lil Wayne. You can create your own playlists, and follow Spotify-created playlists, but generally I just listen to my big stack of music on random.
On the go
Spotify also has an iOS app. It works the same as the desktop app. Generally I just play songs at random, like I do with the desktop app.
When connected to the Internet, you can stream any song on Spotify. You can also sync certain songs to your phone so that they’re available even if you don’t have an Internet connection. I do this so I can listen to My Music anytime.
My favorite headphones are these simple ones from Monoprice. They sound good, and they’re not bulky. When I’m not using them, I can wrap them around my phone and they fit in my pocket without taking up too much space. Also, they stay in my ears. The default Apple earbuds are always falling out of my ears.
In the car, a 2007 Honda Accord, we hacked into the CD changer system using an Enfig car stereo. So basically, we can plug in an iPhone and play Spotify. Sometimes we play from an old iPod. The Enfig is a bit fiddly, and required some installation, but it’s better than dealing with CDs.
A while back, we got Sonos speakers, which are controlled over Wi-Fi. We have a speaker in the kitchen, one in the dining room (connected to some cool old Hi-Fi speakers), and one in the living room. The setup is really easy and you can play music in all the rooms at once, or just a subset of speakers if you want to. You control the music through the Sonos app, which works on your phone and/or on the computer.
One drawback of Sonos is the app isn’t that great. It works okay, but I find it confusing to navigate. It works with Spotify Premium, so you can play any song you want, but you can’t access Spotify’s My Music song list, which is a bummer. Mostly, we play Pandora radio stations, which are free (ad-supported) and easy to access.
Old song files
We had a bunch of old song files that we ripped from CDs years ago, as well as everything we bought on iTunes over the years. I can’t quite take the leap of faith to delete all those files, but to save space, I subscribe to iTunes Match. It takes a snapshot of every song in your library and uploads it to “the cloud”, i.e. an Apple server somewhere. This allows you to delete all the songs from your computer and phone.
If you are connected to the Internet, you can still play these songs anytime from iTunes on your computer, or from your iOS devices. You can also download the songs back to your computer / device as desired. I don’t play these songs much, but for $25 a year it’s useful to know all my music is stored somewhere.