The Joys of iTunes

A couple months ago, I decided to check out my library's downloadable audio books and see what I could find. I love to read and have decided to get back into reading. The challenge I have is that Noah doesn't let me. I have found that he loves to watch things and he loves to really concentrate on things but he doesn't like to be sung to or read to. He starts to cry. I really didn't thing my singing was that bad but ya never know. Either way, I wanted to find a way to read.
I decided that an audiobook was a great way to "read" without reading. I downloaded the software needed to download and transfer the audiobook and within a couple hours (yeah it takes a bit to transfer to the iPod) had 3 audiobooks on my iPod. I listened to the first one. Then the second. It was awesome to be able to "read" while doing laundry or cooking or something.
It was during this time that I was adding some Christmas music to my iPod but for some strange reason, it wouldn't sync. I checked to make sure everything was being added properly and it was but it still wouldn't sync. I found some support sites and sent emails, but no one could tell me why my iPod wouldn't sync. I did find out that iTunes 9 was having issues with the iPod Classics so I assumed that was it. I finally called Best Buy and the Geek Squad guy there told me to uninstall iTunes and then reinstall it. So I did. It didn't work. It still wouldn't sync. I opened up iTunes and decided to do a little investigating. Thats when I found that the tick box to manually manage music and videos was checked off which was fine; but the other tick box to sync only checked music and videos was grayed out. I clicked on the music tab and the tick box to sync music was NOT checked off. Hmm....Curiosity got the best of me so I decided to uncheck the box to manually manage music and then check off the box to sync checked music. That worked! YAY! And then the new problem. Because I had uninstalled then reinstalled iTunes, I now had a pop up telling me that my iPod was synced with a previous library which meant many of the music I had I now had to find and then re-add. I did that. I decided to download another audiobook and realized after putting it on my iPod that having the audiobook requires the user to manually manage music which automatically unchecks the option to sync checked music. I ended up going through that whole deal of re-adding music again.
Last night I had an idea. I went through my music file and found that I had an iTunes folder within an iTunes folder. Today I plugged in my external drive and then decided to completely organize my music. I made a folder for all the music I wanted on my iPod and then categorized it by Gospel, Christmas, Classical, Family, etc and then I went through my music folder and moved the selections to the proper category. After I made sure ALL my music was on my external, I deleted the iTunes folder that was within the iTunes folder and then I deleted ALL the music on my iPod. I also made sure that any music deleted off of my iPod would also be deleted from the iTunes folder. Amazingly after doing this, I now had 13 GB additional free space on my hard drive. Unfortunately, I still had to add back all the music to my iPod. I got alot of it transferred but I still have a lot to go through and add. Main reason is that my music on the external drive is mp3 and iTunes has to covert it to mp4. Tedious but it does the job. The exciting part is now that I have done this, I can add audiobooks without having to worry about the unit not syncing and when I do sync it, I wont have to add music back.
With that said, I am very tired and headed to bed now. Good night!