Which versions of LW and iTunes best?

[goodkid1]

A friend gave me a PC with Vista installed. I would like to know which versions of LW and iTunes would be the most trouble free for the PC. I use "OldApps" for older versions. I got good advice here when asking questions about which versions of LW and iTunes to use on an older Mac Tiger system. I ask the same now for my Vista PC. Just experimenting, I loaded LW 4.14 and iTunes 8.2. But the automatic transfer of music from LW to iTunes I get on the Mac doesn't happen on the PC with the LW 4.14 and 8.2. What is the newest versions of LW and iTunes that work best together on Vista w/o the troubles I hear about LW 5.0, etc.? Thanks