Song data changes and album art not updating

I've been using itunes for a couple of years pretty smoothly, but lately (past 2 months or so), I've noticed a degradation in the performance. When I go to update the album art or other song info for a whole ablum at a time, maybe only 6 tracks are updated. It can take 4 or 5 repeated attempts before it finally "sticks" for some tracks. This also happens sometimes when I'm updating a single track, but there doesn't seem to be any rhyme or reason to which tracks are affected and which aren't.
Other functions are fine: playback, burning, importing, just the maintenance of the data attached to tracks.
My first guess is RAM, I've only got 256 megs, and my library sits a little over 50 gigs. I know upgrading my RAM makes sense on many levels, but I couldn't find any topics with a similar problem, so I wanted to rule out other possibilites too.
Thanks!
Vaio desktop   Windows XP Pro   256 RAM, library on external HD

I think they've all been ripped, and Gracenote didn't have correct or complete info. Not all of the tags were v2.3, but they were v2.2 at least. Was there really that big of a difference between the revisions?
I just tried updating the tags to v2.3, and the same thing happened! Only 3 of the 16 tracks show as having updated to v2.3, the rest are still v2.2, or oddly enough show as none (despite having info displayed in the library and "get info" screens). I bet I can get the remaining tracks to v2.3 after repetition, but it's a pain to have to do the same action 5 times to make it stick.
Not the source of the problem, but a complicating factor was that I tried the wmp11 beta, and it seemed to have stolen the album art from itunes. Those albums which showed up in wmp (only about 15-20% of my collection)were the exact same ones which disappeared in itunes. When I went to repair the album art gaps in itunes is when this issue went from a minor annoyance to a clear sign something was wrong.

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    Message was edited by: KRitchie
    Message was edited by: KRitchie
    Message was edited by: KRitchie

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