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How does a buyer know whether the web site itself owes any money or has any obligations that could transfer with the sale?
The owner of the site may have legal/financial problems, but unless there is a lien placed specifically against the web site, there should be no affect on the transfer.
Obviously the main concern is that the "owner" really does have the legal right to sell the site. You have to do due dilligence to determine that the person is the actual owner and not just a disgruntled employee who's going to disappear with your money.
Do domain escrow services provide checking for these issues or do they just handle the money transfer?
As with any major sale, there should be a purchase contract stipulating exactly what you're buying. Are you just buying the domain name? Are also also buying all the content? What about the customer base? (Can the owner legally turn over all the customer data to you?)
The agreement I have with the company is that if someone buys from my site (that I bought from them for about $USD 250) then I'll get the 75% of retail profit. The biggest issue is getting folk to buy from my site.
Interestingly, the site also sells itself, in that you can buy the site and have your own site name!