Mac, I've been playnig with Knoppix on the box that usually runs Win98 and I'm impressed. If you've got the bandwidth, I'd recommend burning yourself a CD. Unlike other distros it's designed specifically for booting off CD. It uses compression so it comes with ~1.8 gig of software, including open office, web browsers etc... TCP/IP worked automagically. Could be quite fun to stick in a mate's machine to show them Linux. It mounts the hard disk, read-only. It also creates a ramdisk. And it's got WINE so you can run Windows programs.
So anyway, back to the problem in hand: Knoppix has a full Samba on board so you can use smbmount to mount a remote MS box's drives. Alternatively you could run smbd and use an smb.conf in the ramdisk (check the man page for the magic runes for this) if you want to share a drive that way.
Unlike xxcopy, dd does a sector by sector copy when you give it partitions rather than files to copy; so you don't get the 8.3 problem. And I'm assuming that a FAT based filesystem will survive being moved onto a larger partition...
Here's some stuff about using dd across a network, by using netcat (which is new to me):
http://www.rajeevnet.com/tips_hints/...s_cloning.html