iTunes: 10 Things I Hate About You

For the most part, I love Apple's iTunes for Windows. In many regards, it's no where near as polished or nice as Windows Media Player, but, well, I'm an iPod user, so I'm kind of shit out of luck if I want to use anything else, and iTunes is still a damn good media player and manager application. With that said, there's 10 things that really, really piss me off in iTunes from a usability perspective. Some things are Appleisms that never should have been ported to Windows, and others that just plain suck, and I wish there were registry hacks or other workarounds for.

1. Apple's SDK sucks. I'm immensely pleased that Apple opened up facets of iTunes to programmers with their COM interface introduced in 4.5. However, I wish they'd go the next step and allow for more extensibility within the application itself. The plugin SDK opens up some functionality within the application itself, but it requires painful programing and the use of full-screen "fake" visualizations to do anything. I want to be able to right click on a song within iTunes and be able to have it go out and find album art. Sure, there's cool programs like the AI BE program that go to Amazon to find your album art and song integration, but it still requires running a separate program. Maybe if they opened up their SDK to do more, some of my other gripes could be fixed, too.

2. Porting the OS X style selection behavior to Windows. This one bugs the hell out of me on my Mac, so why in the hell do I want this contradictory behavior under Windows. This behavior being that if I am shift-selecting a block of items, if I move up, it doesn't unselect from the selected item, it selects from the top. This drives me up the wall. I understand that when you're using OS X, this behavior should be consistent across applications. But, things don't work this way in Windows, so why did Apple have to port this behavior over?

3. Let me choose how I want to delete files. When I hit 'delete' to kill a block of songs, it pops up with a dialog box that asks [Cancel] [Keep Files] [Move to Trash]. The default is Keep Files. I despise this option. It will remove the files from iTunes, but leave them sitting on your disk. I want either a) Move to Trash to be default b) Keep Files to be removed completely or c) my preferred option: add a check box that says whenever I delete files, it just deletes them. At the very least, I wish it could keep track of files that I used Keep Files with. Often times, I choose this by accident and end up with a bunch of orphan files on my disk. This requires me to go through the time consuming process of having it re-add everything in my music folder only to delete those files again. It's a pain in the ass.

4. Don't stop a synchronization when there's a warning. This happens far too often, I start synchronizing my iPod and walk away. I have a few thousand songs to sync, so it will take a while. I come back after a couple hours only to find a dialog box saying, "Could not sync song X because of Y," with nothing synchronized. This is a non-actionable dialog, I can't cancel my sync and find the file. So, why should it stop a synchronization?

5. While we're at it, I want a log of synchronization problems or warnings. So, synchronization hangs because of, say, a missing file. I fix the missing file. But, oops, there's 30 more missing files. But, I'll have to synchronize again and again and again until I find all the missing files. This is way more painful than it should be.

6. Help me to better manage my library. Why is it I only find out about problem files after I've tried to modify them? I'll rename a bunch of files, and they will have (!) next to them. This requires me to go in and manually locate the files. It's a pain.

7. Internationalization needs work. Why can't iTunes help me to convert non-Unicode localized tags into Unicode? I have written a program to help me with that and plan to use the COM SDK to help tie it into iTunes (see gripe #1), but that's just a band-aid. In addition, I'd really, really love it if iTunes was smart enough to know the difference between A and Ａ (or narrow-A versus wide glyph A). It makes searching a pain in the ass.

8. Inconsistencies between iTunes and the iPod. My iPod is smart enough to sort when The, or A is in the song title. If something starts with The, it will alphabetize it properly (i.e. not put it in the "T" group). Why isn't iTunes smart enough to do this?

9. Broken duplicate checking. Apple fucked this one up. Its duplicate checking used show duplicates based on song title only. Now it shows duplicates based on artist and song title. This stinks. I can have 10 songs that have the same title that are technically the same song (but say, one has an artist's name in Hangul, and the othe ris in English), it won't show as a duplicate. While we're at it, why can't Apple do more to determine duplicates? This is way, way pie in the sky, but why not implement some sort of Musicbrainz-style fingerprinting or other hueristics to determine a duplicate other than simply going by title. Even the title isn't fool-proof (see #7).

10. iPod sharing between computers is more painful than it should be. I sync my iPod in the morning and come to work. The first thing I have to do is place my iPod on manual sync mode on my work computer. Play counts will update properly, but not star ratings. I cannot use party shuffle. I cannot share my iPod library (unless I add my iPod library to my work iTunes). I will then go home and will have to place it back on automatic sync. This sucks. Using my iPod at work should be as simple as using it at home, without having to jump through all these hurdles only to get extremely limited functionality. I'm not asking to be able to easily auto-sync my iPod from multiple locations, I just want to be able to use my iPod at work without having to go through 5 different dialogs and not having anything other than play counts to take home.

iTunes is a great program, but aside from its standard gripes (it's slow, it's ugly, it crashes a lot, it consumes a fuckload of resources, etc), there's some simple usability faux pas that if Apple addressed (or allowed others to fix with a better architecture), it'd make the program much better to use. Maybe even better than Windows Media Player.