The alternative at the time was to buy an mp3 player with no way for normal people to load or buy music. It's precisely because of the lack of hoop jumping that iPod took off. Don't confuse the customer experience with the developer experience. Apple has always considered ease of use for end users a top priority and ease of use for programmers to be a distant nth.
When iTunes came out, there was no way to buy music with it either. It was that way for several years.
Adding to that, when iTunes came out, most people didn't put any thought into ID3 tags. When they imported their music, their library became one big mess.
Windows support was not immediate either. It took some time. I used to use a program written by a student at Williams College. I forget the name. It was more simple and faster than iTunes. Then for a while I used a Perl script. I must admit, in retrospect, Apple knew what they were doing. I just couldn't see the point in iTunes. I doubted whether their $1/song "music store", and forcing users to use it by forcing them to install iTunes, would ever fly.
IIRC correctly most of the older MP3 players didn't need any software beyond what was built into Windows.
Of course this was the era of Windows 95/98 so how well that worked overall it's difficult to say.
No matter how much you might try to excuse it, there is no greater user friendliness
than a device simply identifying as data storage to the OS. It's ridiculous to have
to use a separate program when you could just use your file manager.
That's a consequence of cutting deals with the music industry. Apple had to block users using their iPods as devices for copying music around to enable the iTunes store to work. There are all kinds of trade off in iTunes design, but in the end it's the only significant end to end solution out there, even after all this time. (Kindle Fire is close.)
Oh and anything that involves the file system is not friendly for a surprisingly huge number of users.
>Oh and anything that involves the file system is not friendly for a surprisingly huge number of users.
"User friendliness" in this case also includes developers, who could easily write a
program that interacts with the device. For example, any media player could be used
to synchronize music (if it supports that feature).