ITunes Crash, Too Much Music?

First of all, I was listening to my iTunes with my iPod not having fully updated with iTunes, meaning, not having gotten the latest iTunes music onto the Mini iPod.
Second of all, I deleted about half of my library right before the occurrence.
Then I got a huge file from a friend of mine, containg a lot of music from one artist, two gigabytes worth to be specific. I then transferred the file to my iTunes Music folder, where all of the music is. Then, I went to the Add a Folder option under iTunes, and added the whole Folder of music.
And it worked, it began to play and such.
So I connected my iPod, which can only hold about 4 gigabytes(?), while my iTunes was functioning with about 4.4 Gigabytes worth of information.
Then the entire program froze when I told iTunes to update my iPod and not only remove the old files I had deleted, but as well include the many files I had just added.
Any idea as to what I should do now? It'll take me a long time to sift through the music I just recieved and pick out which ones I wish to delete, so is it possible to pick and choose which music I don't want on my iPod? Furthermore, without freezing iTunes when I connect my iPod to accept all of that music?
Any help would be much appreciated.

RealityMatter:
I think that firstly you should uncheck all of the songs/podcasts/etc. and simply update the iPod so that it has no music. Then you should divide the massive amount of files by 100 or 150 songs at a time and upload them onto your iPod. Seperating the tasks may help with the problem because it won't overload the system by attempting to do too many things at once. If I am wrong with this idea, please, someone correct me. But that is what I would do.

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