I don't know why people consider iTunes as terrible, was there anything better before that? Because the last I checked, if you wanted to get music on your iPod, your only option was that. Considering I used it as a Windows user for many years, it was the only way I could download apps outside of the App Store on the iPod Touch, sync my photos, Outlook contacts, music and videos. And it did a pretty good job at it too. Windows had no actual built in way to do this back in 2009 and they intentionally refused to because they were still trying to compete with Apple.
What made iTunes annoying was numerous updates. I got sick of seeing the Apple software update utility, but outside of that, the program wasn't a problem and did what it intended. How long did the Rio, Nomad Creative, Zune last.