1. Completely unintuitive music organization: iTunes does great with music you buy from the iTunes store, but anything you import from any other source usually has all the completely wrong information attached to it, and you have to edit it one by one. It also doesn't smartly connect artists, if there's a feature artist on one track on your album, then the song gets listed not under "Artist A" but under "Artist A featuring Artist B". What are you doing?!?! It's the same artist, list it with the rest of their songs!!!!
2. Randomly forgets your library or your iPod FOR NO F**KING REASON! Seriously, it's happened at least 3 times where I plug in my iPod and iTunes says "Your iPod is corrupted" then you have to reset it and it take an hour to reload all the music. Oh and even better, iTunes recently just forgot my library. I start it up one day and it says "iTunes library folder can't be found". I look in the music folder and it was right there! But iTunes forgot it! Cue another hour spent importing files and rebuilding my library.
3. Any file that wasn't purchased in the sanctioned iTunes store is handled weirdly: Sorry, not all my music was purchased from the store, I did have CDs back in the day, I've exchanged music with my friends, and I've bought music from other websites. But when I import none-iTunes store music, it duplicated the file, it also sometimes wants to convert it to AAC format, which make the file size bigger, and makes the file a slave to iTunes.
3. They secretly want you to not back-up your files. A few duplicates ended up in my library, so I deleted them, I also accidentally deleted a few purchased songs. Is there some kind of warning window saying "Oh, hey, you're about to deleted some purchased music, are you sure you want to continue?". Of course not, it just goes in the trash. So I realized I deleted 3 recently purchased songs, so I go to the store thinking maybe I can re-download the songs. Surely since they store every tiny bit of information about your purchase, and automatically know when the song is authorized on a new computer, they will let you re-download the song on the same computer you purchased and downloaded the song on to begin with, right? RIGHT?! Nope, no dice. Time to
4. When you do back up your files through iTunes, they do a shitty job: I just got a new computer, so I do the ol' transfer of the files, and I backed up all my purchased music onto a DVD. I upload the music, it's working no problem, oh except the occasional song that just randomly stopped 45 seconds in. iTunes wouldn't tell me what was going on, so I installed a new music player which told me the file was corrupted. Oh, I see, iTunes, I use you to back up my music, and you can't even write it to a DVD properly. So what happens when the files corrupted because of something iTunes did? Well, since there's no way to re-download your purchases, you better just hope the file is still in tact somewhere (luckily I also has my iTunes music on an external hard-drive).
5. Rent movies from iTunes? How about no. $3.99 for new release rentals? You can rent 4 movies from Redbox for that, or just double it and have unlimited movies for a month from Netflix. I'm already trying to get away from iTunes for music purchases, no way will I start renting movies from them.
In short, I know it's a free program, but considering it's created by Apple which prides itself on creating attractive, user-friendly hardware and software, iTunes is remarkably frustrating and unintuitive. The fact that there's no way to recover an accidentally deleted or corrupted file is a flaw that competitors are already taking advantage of (see Amazon's new Cloud Player). I was recently suggested Songbird as an iTunes alternative, so hopefully my days of iTunes frustration are coming to a close. Good riddance.
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