Yeah, with your setup, wi-fi sync will be challenging at best. USB sync is probably the only real workaround. I'll bet the next release of iTunes requires Win7 or greater.
You'll have challenges running iTunes inside an OSX VM, as there's no graphics acceleration for guests yet, but if it does work, just use USB syncing. You're running into bonjour issues (two machines on one IP address). You can try switching to bridged networking, but I suspect it'll still be problematic.