Songs show as okay but become corrupted when played on iTunes?

I'm working with my 64gb iPod Touch 5th Generation.
My family has been known to have problems with computers and therefore iTunes so we decided to take action about a year ago. When we would decide to upload a CD to iTunes, we would download it on the hard drive of our computer then drag it on to a flash drive then if we had to transfer our iTunes to another computer we wouldn't have to download that CD again; we could just put in the flash drive and just 'Add File to Library'. Yesterday, I put some more CDs on the flash drives and today I sat down at 11:00 expecting to be done adding them to the library by one including a lunch break. I was there until four.
I had to wait for almost all of the music files to convert to the correct file format so that took a lot of time. My original plan was to add every song on the flash drives then go back through each artist and delete the corrupted songs (the ones with the exclamation mark [!]) and the duplicates. As I went through after I finished adding them all, I realized that songs that were problem-free last time were now corrupted. Another thing that I noticed which stressed me out the most was the fact that even when a song did not have an exclamation mark, it could still be corrupted. I found that out when trying to play a song and it (the exclamation mark) just popped up next to it with the usual 'Find the location of the track' message. I then realized that I would have to 'play' (double-click) EVERY. SINGLE. SONG. If I wanted to get rid of every unneccessary song. I had 2300 songs and the length of that project just drew the line for me. I figured I would come one here and try to find a solution but I couldn't find a discussion with the same problem.
So here is my official question: How do I prevent the not-corrupted songs from getting corrupted?
Please note that the songs that actually transferred when I sync'd it were a mix of every song I had purchased, some songs that had survived from the last sync, and some new songs from the flash drives.
I am working with Windows XP.
Thank you in advance for the ideas and if at all possible, I would love to avoid having to restart my iPod. My iTunes is 11.0.1.12.

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