Ratings won't update from iPod to iTunes

I know these sorts of questions have been posted before, but all the answers I can find simply seem to say "it should work if you set update to automatic"... Well, it doesn't.
Experimentally I've been putting a few unrated songs from my iTunes onto my girlfriends iPod mini. For iTunes to even allow me drag and drop to the iPod in the first place i HAVE to set it to "manual update". I go off and rate the songs, then come back and plug in the iPod and set it to "automatically update all songs". Here it says there is not enough room on the iPod to put my entire collection (duh...), so I select "no" to the custom playlist it asks to create. Then the songs on the iPod are greyed out and no ratings have been updated in my iTunes.
If it was set to "manually update" the only difference is the iPod songs are no longer greyed. No rating update.
I don't have my own iPod yet. This problem is the only thing holding me back, as the ability to rate your songs away from home is the ONLY reason I would buy an iPod over many of the other, most likely superior, mp3 players out there. For a brand which sells itself on intuitive interfaces, why are there so many people who still can't get this basic feature to work right?
iPod mini   Windows XP Pro  

Experimentally I've been putting a few unrated songs
from my iTunes onto my girlfriends iPod mini. For
iTunes to even allow me drag and drop to the iPod in
the first place i HAVE to set it to "manual update".
There's your problem. Set it to automatic, and choose playlists to be updated. You cannot drag and drop in automatic mode. You cannot update playcounts/ratings in manual mode.
I go off and rate the songs, then come back and plug
in the iPod and set it to "automatically update all
songs". Here it says there is not enough room on the
iPod to put my entire collection (duh...), so I
select "no" to the custom playlist it asks to create.
Then the songs on the iPod are greyed out and no
Set it to "Update Selected Playlists" and just pick a few.
It is normal that the iPod playlist is greyed out in automatic mode.

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