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UNABLE to transfer my music or movies onto iPad! Very annoyed!

So....I have had my iPad 2 for a few months. It was purchased for my dad's company, and he was letting me play around with it and explore it's capabilities. I am very computer savvy and have had tons of experience dealing with Windows and Linux, but this was basically my first experience with the iPad, or anything Apple, for that matter. However, it was pretty easy to figure out, pretty convenient to use, etc.

Lucky for me, and for reasons unknown to me, the company no longer needs this particular iPad and I have recently taken ownership of it. Since it is officially mine, I decided it is time to put my media onto it and take advantage of the iPod feature. Though I have not used iTunes to purchase anything, I use the program on my laptop to listen to music (which I have transferred from CDs), and to watch digital copies of movies that came with DVDs that i bought. However, it has become a huge escapade trying to transfer my content onto the iPad.

After much research, I concluded that 'syncing' transfer data FROM the iPad TO the computer, but not vice versa. The way to transfer data TO the iPad FROM the computer is to simply drag and drop. (correct me if this is wrong?) It seems like it should be simple, but dragging and dropping does not do a thing. For some odd reason, when I drag an entire album to my iPad on the left side of iTunes, I can sometimes get one or two songs to transfer. But that's it. So I have about six random songs on my iPad, all from different albums, because those happened to be the songs that decided to move over. And since a couple songs DO transfer over and show up on my iPad's iPod, I am pretty sure that I am doing the right thing by "dragging and dropping", but I don't understand why most of the content just does not transfer over. I cannot get any of my movies to transfer at all. It makes absolutely no sense and I am completely baffled... and rather frustrated by the whole ordeal.

Is this a common issue? Am I doing something wrong? Is there some major key that I am overlooking?
 
Drag and drop is one method, but may only work if you have manually manage ticked on the ipad, not 100% sure.

Alternatively you can just choose what to sync (apps, music, video, etc), when the ipad is connected to itunes via the tabs along the top, once you select the ipad under devices in itunes.
 
I use GoodReader to transfer my movies and music to the iPad. Then there's no need to deal with that dreadful iTunes program.

Tim
 

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