The last time I jailbreaked my phone was with my Hackintosh. Since im too lazy to fix it after the system updated itself and became no longer bootable I am using my WindowsXP partition to jailbreak the phone to use 3.1.2. Now I just installed iTunes 8.2 in windows and currently going though my OSx86 partition via MacDrive to copy my prefs from iTunes to iTunes in windows. I have ran into one snag so far and lost all of my contacts. I can get that back once when I get my OSx86 partition bootable again.

If all of this works I will create a howto on merge OSx prefs with Windows prefs.

Sounds like everything you are doing is causing nothing but headaches.

As far as the contacts go, they are probably just pulled from address book and not stored anywhere in iTunes.