So I finally broke down and could not find a reason why not to get and iPod. Got a 4G clickwheel 40GB one, but all was not as smooth as I expected.
Bought the iPod on a Saturday at my local Apple Store, and following the manual, I left the iPod charging and went to sleep. The next day, I connected it using the firewire cable to my iBook and nothing happened. Tried the USB cable and iTunes happily recognized the iPod.
Did some googling on that, and some people mentioned that that problem disappeared when they did an update to the latest iPod software, so I downloaded the update from January 11, 2005 and run it. The iPod was happily updated via the USB connection, it asked me to connect it to the power supply (which uses the firewire cable), and then it finish resetting. All seemed well, so I tried using the firewire cable to connect the iPod to the iBook, no luck again. The weird thing is that my iSight camera works just fine with that same port (more on that later).
The next day, I took the iPod to the store, and after some testing, in which they used some of the semi-secret menus (press back when the iPod is resetting to get to them), The Genius in the Bar (sorry could not resist a bad pun) said that the firewire cable seemed OK (worked with his iPod on his Powerbook), so it might be a problem with the iPod’s hardware, so he decided to exchange it and give me a new one. Before I left the store, I connected the new iPod to my iBook, and iTunes saw it, so I ejected and then disconnected it. On the way out, I bought an iPod case.
Again, went home, let the iPod charge and the next morning went to see it, and lo and behold, instead of a battery icon, the whole screen was solid black. I disconnected the iPod from the power supply, and it seemd OK. Tried connecting it with the firewire to the iBook, iTunes did not even acknowledge, nor the OS mounted the iPod. As before, the USB connection worked just fine.
Yet another trip to the local Apple Store, a different person in the Genius bar tested the power supply and found it fubared, he gave a new one. We connected the iPod to it and a nice battery icon showed up. I mentioned the problem with firewire and how the iSight worked fine, but he said that the iPod uses different pins as it was mounted as an external drive. To test that, he took one of the Mac OS X restore firewire disks they got there, rebooted the iBook and held the “option” key, but the iBook did not see the external firewire disk. Great, yet another problem with the iBook (this iBook will suffer a broken keyboard the next day, which was solved a day after by the Apple Store techs. It is good to have the AppleCare plan).
The repair of the firewire port in the iBook means that it needs to be sent to out, and being that I am but a few days away from going to Perú I decided to perhaps do that in Lima, as there are at least 5 Apple certified repair centers there.
Once home, I made sure that iPod was fully charged and dumped via the USB cable about 32GB of music (all of my CDs + a bunch of music bought from ITMS). After that, I let if charge again and started playing music while I was packing. After many hours, the battery power was depleted, but I was not sure about 12 hours had passed, so I let the iPod recharge overnight. The next day, I set it to loop on a group of songs I particularly like (50+ Bossa Nova songs), and starting timing its battery life. The power run out in about 8 hours (7h57m). Perhaps the fubared power supply had messed up with the battery? I will run some battery life tests later to check.
I guess I might need to take the iPod too to be checked while I am in Lima.
Update from 2017/04/20: The iPod still sort of works (though only connected to its power brick), and my elder son (Ken) inherited it about 5 years ago.