bunn, i've had good luck in moving files around on an old ipod via firewire.
I have a couple of FW400 externals that are handy for moving files(and the fastest way to do so, short of target disk mode or gigabit ethernet), but it doesn't help much if the destination computer doesn't have firewire or even the ability to accept a firewire card.
Most every Mac made from about 1988 to 1998 had an external SCSI port, and I can connect an external SCSI ZIP drive to those. It's even handier if they have an internal ZIP drive.
A classic example of where I've made extensive use of ZIPs is when I've downloaded old OSs off of Apple's website. Everything up to System 7.5 is available, but all the downloads are in the form of floppy disk images. The only way I know of to actually
do anything with a floppy disk image requires the use of a computer with a built-in floppy(not an external USB, although I have tried) and a pre-OSX operating system.
In those situations, I use a newer computer-anything from the Quicksilver I'm on now on up to my 2011 Macbook Pro-to download the images. I then dump them all onto a ZIP disk(for computers without one built in, I have a handy bus-powered USB drive). I then fire up my beige G3 into OS 9, pop the ZIP disk in its built in ZIP drive, and use Disk Copy to turn the images into physical floppy disks.
Of course, I could put a USB and Firewire card in the G3(I just got a second beige G3 this past week, and it came with a USB card installed-I also have a firewire card or two lying around) but using the ZIP disk is just as convenient.