There are a few things iTunes does right. It's a decent, non-customizable media player with about half the features of other modern players such as Winamp. Unless you have some good technical knowledge, you're probably stuck using it if you've got an iPod; while the program could easily be better in just about every way, it's not an absolutely terrible application.
But enough praise. I'm here to discuss the numerous shortcomings of this barely passable player:
Hilarious pricing. Songs on iTunes, unless on sale or bought in special bulk packages, cost a dollar a pop. Are you joking me? Physical albums these days have about fifteen songs each on them. In order to download an album of songs, it costs me the exact same amount of money as an actual album, except I don't get the case, the cover, the insert with all the lyrics, and the CD itself to play anywhere I want to. Of course, even if you don't care about those things, you still have to deal with...
Digital restriction. When you download a song from iTunes, it's saved as a protected AAC file, which can only officially be played by iTunes itself or an iPod. You can't send the song to any other computer without converting it using third-party software. After synchronizing your iPod with a certain number of computers (I believe the threshold is 5), the songs then can't be synched any further. Hundreds of other online companies offer music at the same price as iTunes (or much, much less even) but with none of the digital restriction. Also, you can get around the restriction by burning your protected songs to a CD and then writing them back, which just makes me wonder why iTunes would create copy protection with such a gaping hole in the security. It's kind of like building a Death Star that can be destroyed with one cleverly-placed shot.
Customization options. Unlike almost every modern media player, when you first open iTunes, what you see is all you get. The skin is okay-looking, but good luck trying to change it. Plug-ins, you ask? You can get a few visualizations and perhaps some support for Apple-approved media players, and that's about it. Tough break there, newbie. You'll listen to music how Apple wants you to, in all ways. This especially sucks if you're switching over from one of the many more malleable players out there; if you plan on migrating from Winamp, it's going to be a terrible experience.
Playback options. Most of us use the tried-and-true MP3 format. Okay, but what about that odd sector of the world who swears by Ogg Vorbis? How about concert buffs or audiophiles for which the integrity of FLAC is very important? iTunes is going to be miserable for such people because no viable options for them exist.
Sorting options. You can change the order of the sorting columns in iTunes... except for the leftmost column. Why not?! Every other media player ever made has this option. Also, good luck sorting your playlist in the order of Artist -> Song, the traditional method of sorting that almost everyone grew up on. If you sort by Artist, it'll then sort the songs by album under each artist. If you sort by Song, it'll sort all songs by their titles. Why is there no third option?
Too many better alternatives. iTunes isn't a terrible program; if it existed in a rather unpopulated market, it'd be a good option for people. But there are so many better alternatives out there. iTunes doesn't really do anything better than anyone else in the media player market, which makes its grievous faults even more inexcusable.
My advice to any iTunes user is to download a copy of Winamp and enjoy the new freedom of a completely customizable player. It's functional, it works how YOU want it to as opposed to how Apple wants it to, and it even has built-in support for iPod synchronization. Go now.
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