I try to be frugal when I'm handing over my hard-earned money in exchange for entertainment. It's not that I don't buy games, apps, software, services, movies, TV, music, etc. It's just that I have to do it carefully and with plenty of thought given to long-term as well as short-term enjoyment - what I'm getting has to be worth my time.

So when Apple announced a 3 month trial and subsequent pricing for their new Music streaming service, I started thinking about whether it would be worth it for me and my family to use it beyond the free trial.

Here's where I'm at currently with my iTunes music collection.

iTunes Match Math

We pay $27.99/year for a subscription to iTunes Match.
This allow us to store all music we've either bought from iTunes or on CD in the cloud and is accessible from any of our Mac or iOS devices, including our Apple TV.
Playlists, ratings, and song play counts are synced and aren't specific to one user or device - so if my wife removes a song from a playlist, it's removed from all devices.
We can play back music from multiple devices at the same time. No restrictions on how many copies of "Songs of Experience" we can stream at once from all our devices.
I'm the one who does most of the fiddling with playlists so it works out great for me. If my wife was more interested in managing playlists, we'd probably run into conflicting ideas of what should be in the "Best songs of 2014"playlist.
The only way we get more music is if we buy music from the iTunes Store or buy/get a CD and import it into iTunes and "match" it into the cloud.

One important detail, as we'll see later with Apple Music, is what happens if you stop paying for your iTunes Match membership:

Any songs you’ve upgraded or downloaded again are completely safe. The only thing you lose is the central storage — iCloud will no longer stream or download matched or uploaded songs to your devices.

So as long as you download all your songs to iTunes on your Mac, your songs are yours for as long as you have a computer capable of playing MP3s.

Apple Music Math

Apple Music is $9.99/month but in order for both my wife and I to be able to use Apple Music on multiple devices at the same time[footnote]On the non-family plan, if you start playing Apple Music from another device, it automatically shuts off whatever device is currently streaming music.[/footnote] we'd have to pay for the family plan which is $15/month.

Let's break out the calculator.

$15/month x 12 months = $180 per year for Apple Music

Whew. Math is hard.

That $180/year gives you access to almost any music ever made in the history of the world. You get curated playlists made by smart people at Apple Music, access to social connections to artists and friends, and the freedom from ever having to worry that you don't have a copy of Bob Marley's Greatest Hits album for the beach[footnote]Provided that there's a decent internet connection at the beach.[/footnote].

The key difference between Apple Music and iTunes Match is that if you stop paying for Apple Music, all that music is gone. You no longer have access to any of the music.

Owning Music is for Old People

What if instead of streaming music, you bought it? (Gasp!)

The cost of an average album on the iTunes Music Store is $9.99. So instead of paying for Apple Music what if you just gave yourself the freedom to buy an album - or individual songs adding up to as much as $15 - a month?

After a year you'd have 12 new albums of music that you owned.

Any month that you didn't buy an album, you'd have an extra $15 in your pocket to spend or save.

I love the idea of a streaming music service where you can play anything and everything, depending on your mood. Discovering new music without worrying about buying an album that sucks is great. I've had lots of fun listening to albums on Apple Music that I wouldn't have otherwise bought.

What I don't love is the idea of putting money into something and then having nothing to show for it when I stop paying. [footnote]You could compare it to renting a house vs buying. However, mortgages and interest rates are not part of the Apple Music experience. Yet.[/footnote] I'm fine with paying $8/month for Netflix and with the knowledge that if I stop paying for Netflix, I can't watch anymore. But somehow music feels more important than that to me. Digital vs "real" CDs doesn't bother me. I don't care if it's on my computer or on a physical disc spinning in a record player. I want the freedom to be able to stop paying and still enjoy the music I love.

Bottom Line

We'll see what happens in 2.5 months when the Apple Music trial runs out, but I think we'll stick to the old fashioned way of owning our music and running it through iTunes Match. I'm guessing that as part of the negotiations with the music labels Apple had to promise to retire iTunes Match at some point in the future. At which point we'll likely hop on the Apple Music bandwagon.