I have just won an off eBay dispute through Pay Pal - however, what you are thinking of doing is pretty unethical, ie assisting someone in circumventing eBay fees.   A seller is supposed to "advertise" list their item at the price they are happy to accept - he did just that, knowing full well that it might not sell, but obviously hoping it would.   The whole reason you are aware that his item is for sale is because of his "advertisement" on eBay - he got what he paid for.   Probably shouldn't have advertised on an eBay chat forum that you were considering entering into an off eBay sale.... Pretty sure they get a bit cranky about that kind of thing.

I thought if they relist and sells advertising is free anyways. 

It's amazing how little I know about how ebay works. How long have I been here. :^O