Sync iTunes Win(Bootcamp)/Mac using the SAME Library

I know this question has ben asked a lot, but most of these questions are dealing with multiple physical units.

I have a Mac Pro Quad Core that is running Win7 under Bootcamp. Therefore, I am using the same hardware for both operating systems.

I have my iTunes Library (the whole Library, not just music files) pointing to a separate, internal drive. Both the Mac and Windows version of iTunes point to the same iTunes Library on the same drive. The Windows version of iTunes has Library organization turned off (mostly because the external drive is HFS+ and Windows gets cranky with that). To be clear: my iTunes Library lives on a drive that is not my boot drive and is not in my User Account directory.

I am using the Mac OS iTunes to manage, maintain and organize the Library. The PC version of iTunes is strictly used as a jukebox. There is no cross contamination of OSes as far as file acquisition. I even sync my iPhone solely on the Mac side.

For those unfamiliar with Bootcamp, the technology pushes me into either a Mac state or a PC state, I am not running the OSes concurrently.

What I would like is to have whatever file management I do Mac-side be reflected PC side without me having to re-import the Library every time I make a change.

Currently, if I add music on the Mac-side, or if I add comments, or anything else carried in the metadata, the changes will not reflect PC-side. I have to reimport the Library, which wipes my ratings and play count and is very annoying.

I would like to know if it is possible to set up the PC version of iTunes to simply update the Library automatically, so that any change I make on the Mac-side is already reflected in the Windows version. For instance, I manage my play lists by comments - so I have "AOR Classic Rock" as a comment entry. If I add this comment to 10 songs on my Mac, I would like the Windows version of iTunes to just have "AOR Classic Rock" in the comments without me having to reimport the songs that changed.

I do not expect reciprocity, since I don't believe Windows iTunes can change files on a Mac formatted drive, but that's okay. I just want the changes I make on the Mac to sync to the PC.

You would THINK that having iCoud, I could use iCloud to sync all my iTunes settings and my Windows iTunes would mirror my Mac iTunes (at least for playlist, count and ratings). I do not have iTunes Match and am debating if its worth the cost. If iTunes Match will create the sync scenario I am looking for, it may very well be worth it.

Any suggestions would be greatly appreciated.