Old computer, new iPod

I have an old iMac G3, running 10.2.8 and I want to get a new iPod (Video or later), but I would like to know if there is any way I can get the new iPod to work on this old thing. I also have access to an iBook G4. running 10.3.something. I would really like to get it working without buying a new OS/computer, I don't care if I need to run Linux/3rd party apps/Terminal Commands. I also have an external hard drive that is not recognized by the old (10.2) computer, but is recognized by the 10.3 computer. I would like to get it working on the 10.2 computer too, and I think ththey are related.

Yes I know I'm a n00b for not buying 10.3,4, and

Thanks for any help!

I don't know if bumping is allowed here, but it has been a few days.
Thanks

I am afraid you will need to run Tiger to get it to work