Windows connectivity was originally done through MusicMatch (that was bundled w/ Windows iPods). Apple now has iTunes (free download) for Mac & PC, so you don't need MusicMatch.
If you have a firewire card, any iPod will work. Even if you have USB only, any new iPod is fine.
Where are you seeing Win (only) versions? Older used iPods on eBay? Apple is selling iPods with no platform distinction.
IMHO, you should buy only a new iPod. The condition of the battery of a used iPod is always in doubt.