Assorted Problems with iPod Nano 4th gen and iTunes

So i am currently experiencing several problems. Let me break it down so that it might help you understand what's going on.
#1 When dragging music files to my ipod in itunes, an error message popped up stating some sort of file reading/writing error, i forgot exactly what it said.
#2 iPod starts randomly reseting itself when it changes to a new song. sometimes reseting itself right after the main menu comes back up. It also does this while connected to my JVC KD-AVX44 stereo in my car via USB and while listening normally by headphones.
#3 I tried restoring it in itunes, after the restore software was downloaded, an error message appeared stating that the ipod could not be restored.
#4 itunes begins to not recognize iPod
#5 itunes freezed when brought up, still not recognizing the ipod.
#6 itunes crashes? It came up with a window asking for an itunes library to continue, selected just "my music" instead, no files labeled .itl in that. clicked cancel, itunes dosn't come back up.
I'm hoping there's something simple that i'm missing here, can anyone help?

I think i'll try reinstalling itunes tonight, i tried using some of the tips in these articles to reinstall my usb drivers etc, as i still can't get my ipod to restore. apple store will be the next step.
http://support.apple.com/kb/TS1372
http://support.apple.com/kb/TS1539
http://support.apple.com/kb/TS1538
Also, (common question) what's the easiest way to get music into your itunes library automatically if downloading from another source. i just dragged all my previous music from "my music" when i got the nano, i'd just been using WMP before. and i can't seem to find a way to automatically have itunes pick up this stuff. kind of a pain in the behind to drag it all.

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