I stopped using it shortly after, because I missed a lot of the features from the iPhone’s built-in iPod app, especially playlists. Simplify Music 2.0 is a completely different app, and while the new features probably could’ve been introduced via an update to Simplify Media (which many downloaded as a free release when it originally came out), they are significant enough to justify the $3 (on sale, $6 starting May 14) purchase price.

What specifically makes it worth $3? Playlist creation and modification, for one. And you’re not limited to your own library for tracks to add to that, either, so long as your friends also have the Simplify desktop server app running, and have given you share permissions. You’ll be able to browse any library you have access to, search them all by artist, track title, album, etc., and tag any song on any library as a favorite. Taking a cue from a new iPhone OS 3.0 feature, there’s also a scrub bar built in to the app that allows you to search through tracks.

If you’re not interested in these features, and just want the basic streaming capabilities, the original Simplify is still available for $4. As someone who has at least a couple different libraries running on multiple computers, I’m very interested in the new features in Simplify Music 2.0. Frankly, they should’ve been (and still should be) offered by Apple as just something the iPhone can naturally do, but if they’d rather leave it to third-party solutions, Simplify Music will do just fine.

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With it being my most used app, I’ve taken quite a bit of time trying out different add-ons to make the most of iTunes. Below is a listing of 10 apps that I’ve used and feel comfortable saying they’re worth the price you pay for them.

CoverSutra

CoverSutra (previous coverage) is one of my favorite add-ons. It is packed with little features that aren’t immediately apparent when you first start using the app.

A few features include music search, a mini-player, Last.fm integration, keyboard shortcuts, and album cover display.

The $22 price tag seems a tad much, but I’d suggest giving the free trial a run and then deciding for yourself if you can live without it.

Moody

I tend to listen to music based heavily on my current mood, or the mood I’d like to be in. Moody (previous coverage) makes that a piece of cake.

Moody lets you tag your music based on color. The app has a spectrum of 16 different colors to classify your moods. From there, you can pick a combination of colors to create a dynamic playlist based on your mood.

What is even better about this is the fact that it is completely free.

Tangerine

In the same vein as Moody, Tangerine (previous coverage) creates playlists based on the BPM of your songs. So say you wanted to create a playlist for a workout (something more intense with a higher BPM), Tangerine can whip up a playlist for you right on the spot.

Tangerine will set you back $24.95 after the 15-day free trial.

Awaken

I find the sound of a regular alarm clock to be one of the most abrasive and painfully horrible ways to start my day. Awaken helps change that by turning your mac in to an alarm clock.

By tying in to your iTunes library, you can now wake up to something soothing like Sunrise instead of that horrendous, ear-piercing buzzer.

Awaken is well worth the $12.95 (with free updates for life). Give the 14 day free trail a run for the next few mornings and see how you like the change.

Simplify Media

One of the really nice things about living in the dorm rooms back in college was that I had access to the iTunes libraries of hundreds of other iTunes users…effectively expanding my listening options exponentially.

Now that I live in suburbia with no one else on my network except for my wife, I’ve lost that easy access to other music.

Fortunately, Simplify Media (previous coverage) has created a really cool add-on that basically gives you that access back.

All you do is add the username of other Simplify users (who have approved your adding them), and you’ll then be given access to stream their iTunes library just as if it was on your own local network.

Simplify Media is free in every way possible.

Synergy

Synergy is a “classic” iTunes add-on. It has been around for over 5 years and is probably one of the most widely used apps for iTunes.

The latest major release (3.5) was a complete rewrite for Leopard.

Synergy basically adds 3 small buttons to your menubar to give you immediate access to controlling iTunes. It is an affordable $8 and includes a free trial. Be sure to check out the tour.

The Filter

The Filter (previous coverage) is another playlist-creation add-on that almost seems magical.

Simply select a few songs that you are interested in, click on The Filter and an entire playlist is created with other songs you’d probably want to listen to at that point.

The Filter uses “advanced recommendation technology” to create these unique playlists by tying in to The Filter community of other users.

The Filter is free to download and use.

DiscoBrick

I don’t use the iTunes visualizer that much, but sometimes it’s just fun to check out what what your music visually creates.

DiscoBrick takes that one step further and creates some seriously amazing visual effects based on the beat of the music.

DiscoBrick is $10.95 for a single, personal license and up to $55 for a public-use license if you want to use DiscoBrick at parties or other events.

TuneBar

TuneBar picks up where Synergy leaves off. On the surface it’s just a simple iTunes controller. Past that…it’s still an iTunes controller. Ultimately TuneBar is more customizable than Synergy and lets your create your own themes by editing simple HTML.

Is it worth the $4 extra over Synergy? Maybe not. Just depends on how much you’d like to customize your player.

iWow

The iTunes equalizer is quite capable for the majority of iTunes users.

But if the sound controls are quite what you’re looking for, or if you’re looking to make those small headphone or desktop speakers sound better, I’d suggest you check out iWOW.

iWOW is an audio “enhancer”…which basically means it uses different settings and effects to make the audio larger, fuller, and more crisp than what iTunes can do.

iWOW is currently on sale for $19.99 here.

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The name is truly appropriate, I’ve found, as installing and configuring Simplify Media couldn’t be, well, simpler. There are no old-school Stuffit files to contend with; nor does Simplify Media require installing packages or rebooting. In the spirit of Mac simplicity, simply drag the app from the disk image into your Applications folder and run it. Configuration is nothing more than selecting the folder or folders with media you wish to share. The default /Users/username/Music/iTunes is already added to the list, so for most users, no additional configuration is needed.

Sharing Media

Adding friends (and, please, only share with people you know; pirating music and videos is bad for you) is also easy. In the main Media List window (pictured right), click the Invite button and you’re presented with three different ways to invite a friend: a preexisting user’s screen name, by email direct from your account (as opposed to mail from Simplify Media’s server which is more likely to be flagged as spam by a friend), or by copying to the clipboard and pasting, for example, to Twitter, an IM client, or your blog.

When friends join Simplify, they “invite” your screen name. The two of you are connected are able to browse and stream — but not save files from — one anothers’ iTunes libraries. Simplify Media even streams WMA files. Obviously, DRM-locked files of any kind will not play on a remote computer unless that system is authorized to play them.

Is It Legal and Safe?

According to Simplify Media, sharing in such a way is legal because songs cannot be transferred from one person to another, burnt to disc, or accessed when a peer is offline. Also, each person can share with no more than 30 others, thus minimizing both the legal liability and the risk of nasties that can happen when connecting directly with other systems.

Interoperability Is Simple, Too

Those nasties can, actually, present an issue for others or those using Parallels, VMware, or Boot Camp, because Simplify Media is cross-platform and available for Windows as well as Mac OS X. In addition, the developers are working on a version to support both WinAmp and Windows Media Player — not that we Mac folk would care. ;-)

Simplify Media is exactly what has been missing from iTunes for years. This little app is completely free and promises not to spy on you. Running it for three days, I’ve yet to see the first sign of instability, and it handles streaming over 6-Mbps DSL quite well.

The only kickback Simplify apparently gets is that streaming a track pops open a window with links to purchase the currently playing album, should you decide you wish to do so.

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