I just got mine Last Friday for free! I thought for sure it was a scam until they knocked on my door with it... but same problem...
But no, my mac OS (9.2) is too old, so I'm, loading my extensive Cd collection onto a Windoze XP system. What a freaking chore! I blew my whole 4 day holiday feeding the cd's into iTunes and still have 70 or so to go.
And no, you
cannot use the same iPod on both system formats. I knew I was getting the free iPod ahead of time so I tried to start loading CD's onto both my Mac system and the windows system because it takes 20 minutes a pop (the windows laptop doesn't have a USB 2 port and the CD drive's a peripheral). so I had about 50 CD's loaded onto iTunes 2.0.4 on the iMac when I plugged in the iPod to the mac and it didn't even recognise the older version of iTunes, nor could it format the iPod.
I WAS however, able to get a sample program called PCMACLAN at
http://ca.miramar.com/ - the free trial gave 168 hours of usage and I transferred the MP3's to the windows 98 machine (running iTunes 4.7.1.30) and from there onto the XP machine with iTunes. (What a hassle. everyone should use macs) but the program is expensive to buy outright, and I have no idea if it can use a web based PC/MAC connection to go from home to work with teh same iPod for example. you could always just plug your external peripheral speakers into the Headphone jack... that's what I do at work...
In terms of loading, can you burn an mP3 disc from one of the machines with your music and then load them over to the Mac Manually???
If I'd of had a CD burner on the iMac I could have burned the MP3's to a disc and imported them that way. but the sony spressa a friend gave me has no driver that I can find online and she doesn't have the original software...
Anyhow our network has about 5 operating systems on it (soon to be 2 windows OS's, 3 mac OS's and one linux! Ahh, children...) so if you wanna mail me maybe we can figure it out for you.
The windows Machine with XP the had no problem once I had the files on the PC network in loading the files into the iTunes.
Eventually I'll get system 10 and have to reformat the iPod back to mac, but I'm hoping at that point our home based server will be a linux machine and make all nice with the various computers. Then I can just get them off the network server after reformatting.