Ask HN: Why is iTunes difficult?

I dont get everything about iTunes and syncing my iPad. I have Movies, Podcasts and misc footage that I have downloaded. I sync content to my iPad. An Example: I have about 30 TED talks (hey show up under the PosCasts section) that I have on my iPad and when syncing them, they dont all sync to a single TED Talks item and when I click TED Talks it shows all the ones I have... However my Apple Keynotes and events do sync under a single item and when I click it I see a list of the ones that I have. It is sort of counter productive in my opinion. I use my iPad for a log of items. It has become me new device to carry around, have access to all of my stuff. I don't longer lug my laptop anymore. However I miss some organizational features. How can I make iTunes allow me to group things my way?