Here are the newly update ‘09 ready reasons to hate iTunes (and the obvious, logical solutions that would truly open up the gates of legal downloading):

1. Still no WAV file downloads. No support for FLAC, the best compression algorithm available. Even of the iTunes store never sells FLAC it should make the iTunes software compatible with it!

Solution: Allow customers the flexibility to choose the file type (AAC, MP3, WAV and especially FLAC!) and the compression rate and NOT charge an arm and a leg for large WAV file downloads.

2. Those idiotic 30 second samples still create universal irk. Sometimes you don’t even get to the vocals or the hook of a song before it maddeningly fades.

Solution: stream full songs or at least move the sample size up to a full minute.

4. The faulty way iTunes organizes music into folders can be maddening. To access a file when not in iTunes specifically, you have to open several folders to get down to the file itself. Further, if the song is not in iTunes’ database, or is on a soundtrack or compilation, iTunes, randomly dumps it into one of several folders including “Compilation,” “Various” or “Unknown.”

Solution: Create an automated function that detects files that might be classified wrong, not classified at all, or are missing either the act or song name, so that the user has the option to organize them appropriately (along the lines of the very useful “show duplicate songs” function which I do like. This should run once every 2-3 times the program opens or be flexible enough that users can choose how often it runs.

5. Those damn check marks! Say you are ripping several tracks off a CD. When you load it up in iTunes, ever track automatically has a check next to it and you have to laboriously go to a pull down menu to uncheck all. Some folks may like this “everything checked” approach but I would guess that most don’t. It’s a singles world iTunes, get with the program!

Solution: Allow a preferences option where users can opt for “all checked” or “no checked” or alternatively create a button at the top of each album so you can “check all” or “uncheck all.”

7. Not enough flexibility in the arranging of the information columns. For instance, the default is to have the song always in the first column position running left to right. You arrange the rest of the columns in the order you prefer, but you can’t change that first column. This blows when you want to select all and copy to another program (especially useful when making mix CD artwork).

Solution: Duh, complete flexibility with the columns. We want it our way, iTunes, make it so.

9. And on the same tip, view options aren’t sticky! If you load a CD iTunes defaults to a setting that shows: Song Name, Artist, Album, and Genre. View options lets you drop out columns and rearrange the order, but the last several updates have not allowed you to save your preference. Why drop this functionality? It’s all sorts of irritating to change this every time you load a CD.

Solution: Throw a pop up screen asking users if they want to save preferences when a user goes in and makes a change.

9. No ability to sort by more than one criteria. This is insanely maddening for folks with large song collections (I have 18,000 songs, I know, I need a life, but let’s stay on point here!).

Solution: Allow users to sort my multiple criteria just like in a spreadsheet.

10. Cover flow is great, BUT, there are Swiss cheese like holes in it’s functionality. First, if any song is not in the iTunes store, the artwork does not come up automatically, and if you have WAV files on your computer, you can’t even add in the artwork yourself manually. How dumb is that!? Also, in some case, the same cover art will come up multiple times for songs from the same album, even though it should only come up once. In a few cases, there is incorrect artwork in the iTunes default for songs. If this is the case, you can’t correct the artwork yourself or easily report the error to iTunes. In iTunes 9, iTunes has decided to force album covers for songs without any artwork. In theory this is sort of useful as it fills in a few blanks where I had not gotten around to searching for the artwork, but in reality, this automated artwork cram down results in all sort of wrong cover art choices. To fix the errors is a serious pain and in some cases cannot be done. LAME.

Solution: Fix the glitches, add more user friendly functionality to the add your artwork option. Give users the option for iTunes to do a cram down of artwork to songs without any and make it easy for folks to reject incorrect or unwanted artwork thereafter. Artwork is a BIG DEAL. Give users maximum flexibility, iTunes!

11. Converting from one format to another within iTunes is royal pain. In this iPhone world, there is no way to sync a significant sized music collection between computer and phone, especially not one that is WAV based. This requires converting select songs to then load onto the phone or whatever PMP. To do this requires: Edit > Preferences > Advanced > Import > change from default import file type from WAV to MP3 > then select songs > Advanced (From iTunes main page) > Convert to MP3. Then when you are done you have to reverse the process so that the next time you rip something from disc to hard drive you get the WAV file type you want. Seriously. Why put us through this? In iTunes 9, there is a button on the bottom bar at the right edge that gives easier access to selecting the file type and size for importing from CDs, but this same new functionality is not available when compressing a song already on the hard drive. Dumb, right? A half fix is almost worse then no fix because it shows they knew there was a problem and didn’t think through to a full solution. Seriously, does anyone at iTunes have iPhone and huge digital music collections? Dang!

Solution: Add to the advanced tab from the home page a dedicated “Convert” option that always stays that way for ripping from CD or just compressing existing files to a different format or file size.

12. How crap is the new iTunes 9 layout once you go to an artist? Really crap. You used to get a screen size rundown of all songs by that artist or all songs with that name. Now you get this unintuitive less detailed smaller screen within a screen that makes it harder to search. Way to go iTunes, you just made it harder for folks to buy music. Heck of a Job, Brownie.

I feel a bit better now, don’t you?