I've been ripping my CDs lately, using iTunes in MacOS X. iTunes is generally a good and useful program but it has a few correctable annoyances that must be fixed. I really hope the Apple team working on it will address the following issues.

First, reasons to love it. I love software that lets me discover things. In the case of iTunes, it has let me re-discover my music collection, well, at least the CD portion of it (I haven't yet figured out exactly how I'm going to get my 800 LPs digitized... we need smart, net-enabled turntables connected to LPDB(tm)!).

This is only the second (and hopefully THE LAST) time I have fed my CD collection into the CD-drive of my computer. The first time was with My.MP3.com's Beam-it Software back in the wild-west days of early 2000, before the RIAA made me re-discover why I hate record companies. My collection still sits in my My.MP3.com account, and most of it is "locked" -- thanks to lawyers and two hundred million in litigation. So here it is two-and-a-half years later, and I've fed my CD collection back in -- well, I still have a bit to go, but I'm almost done.

iTunes now manages nine thousand (9000) songs from my CD collection -- that's 9000 and counting. Or, 37 gig and counting. I'm sure there are others out there with hundreds of gigs and perhaps some out there with a terabyte or two (we need a better word than tera -- one syllable too long -- my suggestion: "tug", as in "dude, I've got eighty tugs of space, we ought to be able to rip the whole original Star Trek DVD series and have room for the movies as well!"). Anyways, I reached the 37 gig level after learning to modify my behaviors to accomodate a very annoying iTunes. This is not user-friendly software for people building big CD collections. It should be! It can be! I'm sure it will be! But I didn't wanna wait -- so I forged ahead into the world of iTunes 3.0 and found some issues.

Why it's exasperating:
iTunes does several things I find absolutely exasperating.

• iTunes is "front-happy".

  It makes itself the "bring-to-front" application all on its own against my wishes every time I feed a CD into the drive and it starts ripping it. This is bad, bad, bad, in my opinion. When you have 800 CDs in your collection, you quickly make the CD-ripping task a secondary priority -- something you want done in the background. Note that BACKGROUND does not mean HIDE. Does not mean MINIMIZE. To hide or minimize the app because it's jumpy, is making me modify MY behavior instead of having a way (through preferences) to modify ITUNES's behavior. If iTunes' main window is visible on the desktop, but not the front app, trust the user: don't suddenly put the window in front unless the user has specified this is the way it should be, thru Preferences.

  I have my iTunes preferences set such that it is supposed to immediately start ripping the second it realizes I've just put an audio CD in the drive. That's great. It does that most of the time (more on that comment in a moment). Problem is, unless I have iTunes minimized in the Dock, it jumps out in front upon commencing a rip session -- and, as Murphy's Law would have it, this always occurs just while I'm typing in a text editor, or in a Terminal ssh session, or doing some other typing work. Suddenly my typed characters are being intercepted by iTunes instead of the app I was working in. And this does bad things to iTunes. It makes its list jump around, mouse icon go busy, and other stuff. Sometimes if you're not careful you can wind up deleting or changing something in iTunes before you've noticed what's just happened. This is an absurdly bad user experience. The user is right. iTunes' behavior is wrong. But wait. It gets worse.

• More on misbehavior while ripping.

  If you happen to be listening to something in iTunes (I now have some 9000 songs online from my collection, so it's hard not to want to browse my collection and listen to stuff, or create Smart Playlists which are great), and you insert an audio CD for ripping, you'd think iTunes couldn't misbehave as it's already the front app window on the desktop. But nooooo.... it has to jump out of whatever pane or mode you're in in ITunes and jump to the "look ma, I'm ripping a CD!" page, showing the tracklist of the CD it's starting to rip. AAAAGGHH. Apple: this is very very bad.

  [Recommendation] Apple, you need to add a preference setting to [ ] Keep iTunes app in the background when a ripping operation begins. Furthermore, it should not kick you out of the mode you're in if you're actively doing something else in iTunes. This is supremely annoying. Fix it.

• Dialog Box Design Inconsistency
  Speaking of Smart Playlists: Apple, you have a design inconsistency that needs addressing on the Smart Playlist dialog box. Create a new Smart Playlist. Go to the Advanced tab. Type something in for the first search criteria. See the screenshot below for what this dialog looks like. (I'll get to that highlighted minus button in a moment.)

  

  Now press the "+" button to create more search criteria. Presto! You get a second line of search criteria to specify. That's great! Now, type in your second criteria and press OK. Right? Well, that's what I did. See the image below for an example of an expanded Advanced dialog:

  

  I can't believe I'm the only user who missed the sneaking insertion of that little pulldown menu at the upper left (see highlight). It took a long while before I found out why my Smart Playlists were never selecting the songs I wanted: I'd created a Smart Playlist where the first criteria was "Artist name matches 'Guided by Voices'" and a second criteria where the "Artist name matches 'Robert Pollard'". I called this Smart Playlist "Guided by Pollard." But I noticed it never showed Robert Pollard's CDs. Only Guided by Voices'. I'd never noticed the change in the upper left part of the dialog until someone pointed it out to me that that new pulldown was there.

  I consider this a design inconsistency because the way things are normally done in Aqua dialogs is to disable and gray out those capabilities which are not usable at the time. Notice how in the first image above, the minus-sign button is grayed out -- why? Because you only have one line of criteria, and one is the minimum. Fine. So it's grayed out. As it should be.

  The dialog pulls a surprise on the user when you click on the "+" button. It modifies the existing dialog box sentence from "Match the following condition:" to "Match all/any of the following conditions". Yikes! From out of nowhere! Is the user expecting this, when the standard is "enable and un-gray-out those UI controls which now make sense and should be usable by the user?" No, the user's not even looking over at the upper-far-left. Why should a user look up there? Why should the user expect such weird behavior? Apple, what did usability testing reveal? Again, I'd be amazed if it was just me who missed that pulldown switcheroo.

  I understand that graying out the "any / all" thing causes grammatical hurdles to be overcome with the "Match..." sentence. So deal with the hurdles and do the right thing for the user. The current way is not the right way, in my humble opinion.

• iTunes forgets your preferences
  This one is very strange. Every now and then, about every 10th CD that I rip, I find that after I've inserted the CD, and Finder has recognized it as an Audio CD, and it has shown up in the "Sources" column within iTunes --- all this is expected behavior -- it just sits there and the CD doesn't get ripped. Even though I have Preferences set to start ripping the moment I insert an audio CD. And I have it set up to "use the Internet" when necessary, and use CDDB to get titles. And I have it set to eject the disk when the ripping is done. But about every 10th ripped CD, I find that iTunes "forgets" to do these things. I have to manually click on the "import" icon, to fire up the ripping operation. And then I have to manually eject the disk. The weird thing is, I find iTunes seems to "remember" my preferences next time! And so it goes for about 10 more rips, and then sure enough, it forgets. D'oh!