You can't sync the same iTunes library with multiple iPods, but there are ways to use iTunes with multiple iPods, as seen
in Apple's KB.
If you don't use iTunes at all, and use something like
YamiPod instead, you can transfer music any way you like - sync it all with two iPods, take music off one iPod and put it on your computer or another iPod, setup different playlist syncs...
To answer your second question - if by "iPod for Mac" you mean an iPod formatted with a Mac to use the HFS+ (Mac OS Extended in Disk Utility) filesystem, then
no, you cannot use it on a Windows machine. You should format all your iPods using FAT32 (MS-DOS in Disk Utility) to ensure intercompatbility with any OS. FAT32 will work with Windows, OS X, and Linux.