Downloading artwork from itunes store / web into itunes & ipod

I just got my 1st ipod. I'm trying to update so artwork will appear in my itunes & ipod. I discovered the get album artwork tab in the advanced section of itunes and that's great but it does not always download properly. I then discovered in some cases if I word my album titles exactly as the itunes store it will then download the artwork. i also found the apply tab in the ipod music folder though it works a little funny. I have to click on and off the artwork button before the apply button will show up without being greyed out.
My question is 2 fold.
How do you get album artwork on to your ipod & itunes together?
I manually manage my music so now the changes I made to my itunes are not corresponding to my ipod. Do I need to 'sync' all music in order to do that ? If so , should I click restore and start from scratch? I have almost 4000 songs right now.
Also I would like to download images? from google of artists albums or photos but cant' figure out how to get it into itunes and ipod....
Any help is appreciated.

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