ITunes crashes upon syncing music to iPhone 3GS iOS4

I recently bought an iPhone 3GS and upgraded it to 4.1. Whenever I try and sync my music, iTunes will crash - I get the "iTunes has encountered an unexpected error and has to close" message, with the Windows report screen popping up and all that. This is only when I sync my music - applications and contacts sync fine (I do not sync videos/photos/voicemails so I have those all unchecked). I only sync one selected playlist (not my whole library).
I am using iTunes 10, running on Windows XP. I have uninstalled and reinstalled numerous times (including downgrading to 9.2 at one point) but I continue to get the same result - iTunes crashes upon syncing music. I just did a fresh restore, and this has not fixed the problem.
I have tried splitting up my 550 song playlist that I normally sync to my iPhone, but when I did this (it was only about 250 songs) iTunes crashed again towards the end. It has been crashing whether or not I have the "Convert to 128 kbps AAC" checked or not. It crashes somewhere in the middle of "Copying X out of X."
Note As of typing this, I successfully synced a separate 58-song playlist WITH "Convert to 128 kbps AAC checked." However, I then tried to sync a different 61-song playlist WITHOUT that checked and iTunes proceeded to crash. After this, I tried syncing the 58-song playlist again WITHOUT the Convert checked and it synced perfectly without crashing.
Recap:
Playlist #1 (550 songs) - Crashes WITH OR WITHOUT convert checked
Playlist #2 (58 songs) - Syncs perfectly with or without convert checked
Playlist #3 (61 songs) - Crashes without "Convert..." checked (have not tested with "Convert..." checked, it's late and I have to head to bed soon and I want to get this post up).
Considering this information, would it be reasonable for me to assume that it's some of the songs in my library that are making iTunes crash? If so, how the heck am I supposed to figure which songs are causing this? I really hope I do not have to sit here as iTunes syncs and watch our for every song it crashes on...
Does anyone have any suggestions? I've scoured these boards but I haven't found anyone with the same situation as me, and thus no answers.
So frustrated. Even my old iPhone 2G on OS 3.0 syncs my music perfectly!!

I am back to attempting to sync my music. iTunes continues to crash on certain songs, however I have also noticed another problem - each time I attempt to sync my main playlist (after deleting the song it crashed on last time), it will say Copying X out of like, 96 or some number that is nowhere near the real count of songs on the playlist.

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