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The Digital Download Is Dead:

Yet despite its omnipresence, iTunes hasn't aged well. Unlike most Apple products, it's gotten slower and more unwieldy over the years. The Windows version is the most annoying program I use on a regular basis. (I don't find the Mac version much more pleasant.) For one thing, it requires constant upgrades. These days the best desktop apps refresh themselves automatically; Chrome, Google's fantastic Web browser, remakes itself without any user input—you start it up and suddenly there are new features delivered from afar. iTunes takes the opposite tack: It wants to be upgraded about twice a month, and it demands constant attention during the process. You've got to approve the 80-plus-megabyte download, you've got to click several times as it installs, you've got to agree to a new license, and you might be asked to reboot your computer. And for what? Most upgrades result in no discernible improvement.

The worst part is syncing my music and photos with my iPhone and iPad. I usually try to do this when I'm leaving the house—in other words, when I'm in a hurry. iTunes doesn't care. It takes 30 seconds or so to identify my device, then several minutes to sync, and it's not unusual for the program to run into some kind of problem along the way, requiring me to start over. All this hassle seemed tolerable back in the days before Wi-Fi, but now it's anachronistic. It's 2010—why do I have to plug anything into anything to get files from my computer onto my phone?