A few months back I sold my iPad 2 on eBay when I purchased a 3G version. I had forgotten to check the box to ship only in countries I ship to and a guy from Russia won the auction. He e-mailed me and I told him of the mistake, and how I had heard negative stories about shipping to Russia. He had over 400 positive feedback, so I didn't cancel the transaction. He sent me a very long e-mail of everything I needed to do though. Basically you have to secure the package as tightly as possible in a box. Bubble wrap and bubbles in the box to make sure even if the box was slightly punctured nothing could be removed. Then you tape the entire outside of the box so that if the tape would be broken you would know the box was tampered with. And on the customs claim form you don't put the name of the item (in my case iPad) you put a general term, such as "mobile communication". He received the package in a week and I was left positive feedback.
I'm glad he had helped me through the transaction and everything worked out. I would avoid shipping overseas, I think in my case I got extremely lucky.