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If someone asks me what I like most about iTunes, I’m hard pressed to come up with an answer.  Ask me what I don’t like, and I’ve got a fairly extensive list.  My first and largest beef is that iTunes limits what you can buy based on the country you’re in.  There is absolutely no good reason not to make the entire catalogue of what is available in every country available to all.  iTunes is cumbersome to update, and frequently fouls up meta-data from songs, along with album art.  It is also sonically quite poor, as I first noticed when I had to rely on a pair of headphones and my laptop instead of my home amplifier and speakers.  A few internet searches later and it quickly became apparent that I certainly wasn’t the only one grousing.  I’ll spare you the tedious details, but basically the software guts of iTunes just don’t do what is needed to make your music come alive.  There are four things you can do to improve the quality of your listening experience:

1) Improve the quality of your music
2) Improve the quality of your headphones
3) Improve the quality of your software
4) Improve the quality of your hardware

This is what I did to improve things, step by step.
1) The first step may seem obvious, but it’s not as easy as you think.  The Apple audio codecs and various MP4a, MP3, etc. formats aren’t that great.  A CD is a far better option, or music directly ripped from a CD into a lossless state such as FLAC or ALAC.  Even better is to go beyond CD quality and into a studio master.  The first few FLACs I used were a noticeable step up in quality.  Going onto a site like QOBUZ and getting studio masters made yet another step up.  Naturally the quality of the producer and his skill are primordial.  Buying from iTunes just isn’t that great, there is too much sonic material lost in the crunching process.
2) There simply isn’t scope here to go into every kind of headphone possible.  Generally speaking I divide headphones into three categories: ear-buds, closed, and open.  Open headphones are not an option for the traveller, and so I don’t bother with them here.  Buds are the space-saving option, but I find them uncomfortable for long periods of time.  My left ear doesn’t seem to like them either, spitting them out.  So, I settled on a good pair of closed headphones.  I dismissed the trendy(Dr. Beats especially) and tried to look for something sonically massive with sufficient separation.  After a number of tries at the local audio shops (Sony, Sennhauser, Seinheiser, etc.) I decided to pick a budget and characteristics and see what matched.  To my surprise, I ended up with an option I hadn’t even known existed, PSB.  I knew of their speakers, but they had recently had a go at headphones.  The model is called the M4U-2, and I decided to buy it without even trying it, reasoning that I could return them if they weren’t up to snuff.  Not only were they great sounding, but they were also noise-cancelling, something which was to save my sanity during several hours of travelling by Globemaster.  They are also extremely comfortable, even while wearing glasses.  They come in a sturdy case with lots of extra parts, and function even without batteries.  Faults are that they are a bit on the large side, and perhaps not the most stylish.  But those faults become irrelevant when faced with the most important point: sound quality.
3) There is a lot of software out there.  I made my decision based on the fact that I wanted to continue to use iTunes as the “organizer,” and that I was going to buy a DAC and needed something that would work with that.  A few hundred reviews later, I settled on Audirvana Plus based on a reasonable price and reviews written by people who liked a variety of music.  Also, it completely cuts sound access to all programs other than itself.  iTunes before had been subject to random urps and bleeps while other RAM and CPU hogs worked in the background.  I have not had anything other than continuous, uninterrupted music since I bought Audirvana.  Also, in my opinion, music sounds better spaced, and more three dimensional.  Instruments are more clearly separated and identifiable.
4) A DAC was bought on the same principles as (3), I ended up getting the AudioEngine D1.  It’s small, portable, and suited the bill for a traveller, being affordable and sturdy in construction.  When I wasn’t travelling, I could use it with my iMac.  It also worked with the afore-mentioned Audirvana Plus, and I noticed further clarity in playback.  It is often tempting to think things are better just because they sound different, but every once in a while I go back to my previous setup and instantly hear the difference.  It’s not just an increase in volume/output, it’s a massive change in clarity and sonic landscape.

Each of these points are important on their own, and it would be difficult to argue that any one is more important than the other.  There are many solutions to the iTunes problem, and I would encourage you to seek out a sonic solution of your own.  Good music shouldn’t be ruined by the poor software and recordings available through iTunes, however convenient it may be.