It's quite well known Jobs fought the Windows version of iTunes tooth and nail.
His theory was that the iPod was so great and since it was Mac only for quite a long time, both products would feed the larger Apple machine.
If people lusted after the iPod, they would in turn purchase a Mac just in order to own an iPod. In the Jobs bio, sounds like he clued in eventually and realized that the single digit market shares the Mac has/had was not going to suddenly balloon to 90% market share just because their MP3 player was so much better that the competitions.
I tried every MP3 player under the sun, and found all the software that came with them to be complete crap. That still wasn't enough to make me want to buy a Mac just so I could own an iPod, but I did pick up an iPod once the Windows version of iTunes launched.
I've got a lot of gripes about the way Apple has always done business, but it simply cannot be underestimated how great of a solution the iPod and iTunes combo was when it hit Windows vs. the other products. It was just so, so much better, warts and all. Only other MP3 player I even liked remotely as much as the iPod/iTunes combo was the second gen Zune, and unfortunately the one I bought died about 8 weeks after I bought it and MS refused to warranty it, despite the fact the hard disk in it outright packed it in due to no fault of my own :/
I still however despise the locked down, walled garden iTunes ecosystem.
I recently got a Galaxy S3, and went to transfer all my old iPhone media to it, only to find that all my purchased books were entirely DRM'ed from Apple. Ended up torrenting un-DRM'ed versions just to be able to use them on the Android device, which was inconvenient and I shouldn't have to be forced to essentially steal things I already paid for once.