So I fire up iTunes, and see there are 17 updates for my iOS apps. I click on the Apps sidebar option, then click on the little 17 Updates Available link in the lower right. I then click the Download All Free Updates button in the upper right. The Enter Password box pops up. I enter it, then switch back to browsing the web while it updates. I switch back to iTunes a few minutes later greeted with a Some of these apps contain age restricted material, please click OK to continue box. I click OK, switch back to browsing.

I switch back later, You've used iTunes on another computer recently, please verify your billing information. I enter my credit card’s CSD, click OK, task out. Back again later, it wants my CSD and my salutation. I enter them, task out. Task back, nothing is happening. I click Download All Free Updates again. I’m now back at step 1.

This time I babysit iTunes through all the steps in sequence, though this time there’s an extra step 4 in there (unsure how that happened).

Ideas

I know you have some UX guys working for you Apple; Perhaps you could throw them at this problem for a while? My thoughts:

• Make iTunes more responsive. I kept tasking out because of the huge lag between clicking OK and actual things happening.
• Keep my apps up to date, automatically, in the background. At least make it an option. And please, delta sync.
• Get rid of the age restricted warnings. Ask me once, per account (or even per app), and that’s it. Never ask me again.
• Remember where I am. If the user happens to sit at the Enter password to continue box for 10 minutes, comes back, and clicks OK… continue with what they asked you to do 10 minutes ago, don’t just sit there.

Its my sincere hope that somewhere deep in the bowels of Apple, there’s a skunkworks team that has spent years rewriting iTunes from the ground up. Its responsive, easy to use, performs simple tasks with little to no effort, and doesn’t require holding down option to delete a song from within a smart playlist. Any day now, it’ll drop. Please.