How can I synchronize two iTunes Libraries on two platforms (Windows & Mac)

I have a MacBook running both Windows XP Pro (Boot Camp) and Mac OS 10.4.9 and I have installed iTunes on both platforms. I have my iTunes Library and songs on an external drive (which I can "see" in Windows via MacDrive), and which I wish to keep in place to save space on my MacBook. Trouble is I cannot get my Windows iTunes to recognize the song files on my Maxtor external drive, even when I point iTunes to these files in the "Advanced" pane of Preferences.
How can I utilize the one song folder by synchronizing the two sets of iTunes so I can listen to music on whichever platform I happen to be working on?
I have tried placing an alias of the iTunes song folder in my iTunes folder in "My Music" in Windows but this does not work.

I agree with Chris CA that this is the way I would *expect* iTunes to behave.
When I look at iTunes from my account (my music is in ~/Music/iTunes/ and not available to my spouse's account), I can see in my music library all my rips and my purchases, just as I would expect. I can use Store>View My Account (<myAppleID>) and all is as expected. Home sharing is NOT on.
Doing the same from the other account is not much different, actually. Nothing in the library yet, of course. Store>View My Account (<herAppleID>) also works. I CAN authorize my computer to play her music. I CAN view her iTunes purchases. When I attempt to download the purchases to HER library, though, I get the following dialog box:
Now I interpret this to mean that this computer (mine) will not download from a different AppleID (also mine) for 90 days. Is that [interpretation] correct?

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